No renderable structure data available
CC1=C(C=CO1)CO[Si](C(C)C)(C(C)C)C(C)CChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | (2-methylfuran-3-yl)methoxy-tri(propan-2-yl)silane |
|---|---|
| IUPAC Name | — |
| CAS Number | 137628-52-5 |
| Database ID | 11043781 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
(2-methylfuran-3-yl)methoxy-tri(propan-2-yl)silane (CAS 137628-52-5) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 11043781
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-6e6bdc4608174b92aee2087e45432ad6Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-d67ddc3032a94e8e8257b3420cc86ac0Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of triisopropyl-(2-methyl-furan-3-ylmethoxy)-silane (14) (10 g) in tetrahydrofuran (250 mL) was cooled to −78° C. with stirring, and then sec-butyllithium (1.3 M in cyclohexane; 37.25 mL) was added drop-wise over 10 mins. After stirring for 45 mins at −78° C., the cooling bath was removed for a period of 15 mins then re-introduced. A solution of N,N-dimethylformamide (14.4 mL) in tetrahydrofuran (25 mL) was added drop-wise and the resulting reaction mixture was stirred at −78° C. for a further 2 hours. The reaction mixture was allowed to warm to room temperature and then poured into saturated ammonium chloride solution (150 mL). This mixture was extracted with diethyl ether (2×350 mL), and the combined organic extracts were washed with water (500 mL) and brine (500 mL), dried, and concentrated in vacuo to give compound 33 as an amber coloured oil. LC/MS System A: Rt=4.86 mins. After stirring for 45 mins at −78° C. the cooling bath was removed for a period of 15 mins then re-introduced A solution of N,N-dimethylformamide (14.4 mL) in tetrahydrofuran (25 mL) was added drop-wise the resulting reaction mixture was stirred at −78° C. for a further 2 hours This mixture was extracted with diethyl ether (2×350 mL) the combined organic extracts were washed with water (500 mL) and brine (500 mL) dried concentrated in vacuo
Source ID: ord-bdff4e8f0cec49599ac810bafa153c7eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of triisopropyl-(2-methyl-furan-3-ylmethoxy)-silane (14) (10 g) in tetrahydrofuran (250 mL) was cooled to −78° C. with stirring, and then sec-butyllithium (1.3 M in cyclohexane; 37.25 mL) was added drop-wise over 10 mins. After stirring for 45 mins at −78° C., the cooling bath was removed for a period of 15 mins then re-introduced. A solution of N,N-dimethylformamide (14.4 mL) in tetrahydrofuran (25 mL) was added drop-wise and the resulting reaction mixture was stirred at −78° C. for a further 2 hours. The reaction mixture was allowed to warm to room temperature and then poured into saturated ammonium chloride solution (150 mL). This mixture was extracted with diethyl ether (2×350 mL), and the combined organic extracts were washed with water (500 mL) and brine (500 mL), dried, and concentrated in vacuo to give compound 33 as an amber coloured oil. LC/MS System A: Rt=4.86 mins. After stirring for 45 mins at −78° C. the cooling bath was removed for a period of 15 mins then re-introduced A solution of N,N-dimethylformamide (14.4 mL) in tetrahydrofuran (25 mL) was added drop-wise the resulting reaction mixture was stirred at −78° C. for a further 2 hours This mixture was extracted with diethyl ether (2×350 mL) the combined organic extracts were washed with water (500 mL) and brine (500 mL) dried concentrated in vacuo
Source ID: ord-bdff4e8f0cec49599ac810bafa153c7eConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of triisopropyl-(2-methyl-furan-3-ylmethoxy)-silane (14) (5.0 g) in tetrahydrofuran (15 mL) was cooled to −78° C. with stirring. This solution was treated drop-wise with n-butyl lithium (2.5 M in hexanes, 8.94 mL). The resulting solution was warmed to 0° C. and allowed to stand for 30 minutes after which a solution of dried zinc chloride (3.04 g) in tetrahydrofuran (10 mL) was added and the resulting solution allowed to stand for a further 1 hour at room temperature. Concurrently, a second reaction vessel was charged with tetrahydrofuran (10 mL), nickel(II) acetylacetonate (120 mg), and triphenylphosphine (122 mg) and cooled (−5° C.). Ethyl bromoacetate (1.03 mL) was added to this mixture, followed by the addition of the previously prepared solution of the furyl-zinc chloride. The resulting reaction mixture was allowed to warm to room temperature then stirred for a further 16 hours at room temperature. The reaction was quenched by the addition of saturated ammonium chloride solution (100 mL) and extracted with ethyl acetate (3×150 mL). The combined organic extracts were successively washed with water (200 mL) and brine (250 mL), dried, filtered and concentrated in vacuo. The residue was purified by flash chromatography using a gradient elution (diethyl ether/petroleum ether (40-60°) 1:49 to 1:25 by volume) to give compound 29 as a clear oil (1.44 g). LC/MS System A: Rt=5.16 min. to stand for a further 1 hour at room temperature cooled (−5° C.) The resulting reaction mixture to warm to room temperature then stirred for a further 16 hours at room temperature The reaction was quenched by the addition of saturated ammonium chloride solution (100 mL) extracted with ethyl acetate (3×150 mL) The combined organic extracts were successively washed with water (200 mL) and brine (250 mL) dried filtered concentrated in vacuo The residue was purified by flash chromatography a gradient elution (diethyl ether/petroleum ether (40-60°) 1:49 to 1:25 by volume)
Source ID: ord-787570d1d6d748748887de43d759e0c5Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of triisopropyl-(2-methyl-furan-3-ylmethoxy)-silane (14) (5.0 g) in tetrahydrofuran (15 mL) was cooled to −78° C. with stirring. This solution was treated drop-wise with n-butyl lithium (2.5 M in hexanes, 8.94 mL). The resulting solution was warmed to 0° C. and allowed to stand for 30 minutes after which a solution of dried zinc chloride (3.04 g) in tetrahydrofuran (10 mL) was added and the resulting solution allowed to stand for a further 1 hour at room temperature. Concurrently, a second reaction vessel was charged with tetrahydrofuran (10 mL), nickel(II) acetylacetonate (120 mg), and triphenylphosphine (122 mg) and cooled (−5° C.). Ethyl bromoacetate (1.03 mL) was added to this mixture, followed by the addition of the previously prepared solution of the furyl-zinc chloride. The resulting reaction mixture was allowed to warm to room temperature then stirred for a further 16 hours at room temperature. The reaction was quenched by the addition of saturated ammonium chloride solution (100 mL) and extracted with ethyl acetate (3×150 mL). The combined organic extracts were successively washed with water (200 mL) and brine (250 mL), dried, filtered and concentrated in vacuo. The residue was purified by flash chromatography using a gradient elution (diethyl ether/petroleum ether (40-60°) 1:49 to 1:25 by volume) to give compound 29 as a clear oil (1.44 g). LC/MS System A: Rt=5.16 min. to stand for a further 1 hour at room temperature cooled (−5° C.) The resulting reaction mixture to warm to room temperature then stirred for a further 16 hours at room temperature The reaction was quenched by the addition of saturated ammonium chloride solution (100 mL) extracted with ethyl acetate (3×150 mL) The combined organic extracts were successively washed with water (200 mL) and brine (250 mL) dried filtered concentrated in vacuo The residue was purified by flash chromatography a gradient elution (diethyl ether/petroleum ether (40-60°) 1:49 to 1:25 by volume)
Source ID: ord-787570d1d6d748748887de43d759e0c5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of triisopropyl-(2-methyl-furan-3-ylmethoxy)-silane (14) (10.0 g) in tetrahydrofuran (300 mL) was cooled to −78° C. with stirring was treated drop-wise with sec-butyllithium (3.0 M in cyclohexane, 37 mL). After 1 hour the reaction mixture was treated drop-wise with a solution of methyl chloroformate (5.2 g) in tetrahydrofuran (30 mL) over 10 mins and stirring was continued at −78° C. for 1 hour. The reaction mixture was then treated with saturated ammonium chloride solution (300 mL) and allowed to warm to ambient temperature. The two layers were separated and the organic phase washed with brine (300 mL), dried and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate/pentane (1:9 by volume) to give compound 15 as a clear oil. stirring The two layers were separated the organic phase washed with brine (300 mL) dried concentrated in vacuo The residue was purified by flash chromatography eluting with ethyl acetate/pentane (1:9 by volume)
Source ID: ord-277331fad4044dd2a6dd5ddd5c8d539eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of triisopropyl-(2-methyl-furan-3-ylmethoxy)-silane (14) (10 g) in tetrahydrofuran (250 mL) was cooled to −78° C. with stirring, and then sec-butyllithium (1.3 M in cyclohexane; 37.25 mL) was added drop-wise over 10 mins. After stirring for 45 mins at −78° C., the cooling bath was removed for a period of 15 mins then re-introduced. A solution of N,N-dimethylformamide (14.4 mL) in tetrahydrofuran (25 mL) was added drop-wise and the resulting reaction mixture was stirred at −78° C. for a further 2 hours. The reaction mixture was allowed to warm to room temperature and then poured into saturated ammonium chloride solution (150 mL). This mixture was extracted with diethyl ether (2×350 mL), and the combined organic extracts were washed with water (500 mL) and brine (500 mL), dried, and concentrated in vacuo to give compound 33 as an amber coloured oil. LC/MS System A: Rt=4.86 mins. After stirring for 45 mins at −78° C. the cooling bath was removed for a period of 15 mins then re-introduced A solution of N,N-dimethylformamide (14.4 mL) in tetrahydrofuran (25 mL) was added drop-wise the resulting reaction mixture was stirred at −78° C. for a further 2 hours This mixture was extracted with diethyl ether (2×350 mL) the combined organic extracts were washed with water (500 mL) and brine (500 mL) dried concentrated in vacuo
Source ID: ord-20a364c83cf641f6931b116530e43300Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of triisopropyl-(2-methyl-furan-3-ylmethoxy)-silane (14) (5.0 g) in tetrahydrofuran (15 mL) was cooled to −78° C. with stirring. This solution was treated drop-wise with n-butyl lithium (2.5 M in hexanes, 8.94 mL). The resulting solution was warmed to 0° C. and allowed to stand for 30 minutes after which a solution of dried zinc chloride (3.04 g) in tetrahydrofuran (10 mL) was added and the resulting solution allowed to stand for a further 1 hour at room temperature. Concurrently, a second reaction vessel was charged with tetrahydrofuran (10 mL), nickel(II) acetylacetonate (120 mg), and triphenylphosphine (122 mg) and cooled (−5° C.). Ethyl bromoacetate (1.03 mL) was added to this mixture, followed by the addition of the previously prepared solution of the furyl-zinc chloride. The resulting reaction mixture was allowed to warm to room temperature then stirred for a further 16 hours at room temperature. The reaction was quenched by the addition of saturated ammonium chloride solution (100 mL) and extracted with ethyl acetate (3×150 mL). The combined organic extracts were successively washed with water (200 mL) and brine (250 mL), dried, filtered and concentrated in vacuo. The residue was purified by flash chromatography using a gradient elution (diethyl ether/petroleum ether (40–60°) 1:49 to 1:25 by volume) to give compound 29 as a clear oil (1.44 g). LC/MS System A: Rt=5.16 min. to stand for a further 1 hour at room temperature cooled (−5° C.) The resulting reaction mixture to warm to room temperature then stirred for a further 16 hours at room temperature The reaction was quenched by the addition of saturated ammonium chloride solution (100 mL) extracted with ethyl acetate (3×150 mL) The combined organic extracts were successively washed with water (200 mL) and brine (250 mL) dried filtered concentrated in vacuo The residue was purified by flash chromatography a gradient elution (diethyl ether/petroleum ether (40–60°) 1:49 to 1:25 by volume)
Source ID: ord-0bc2aef8246b4881a449c43831cb7ec6Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of triisopropyl-(2-methyl-furan-3-ylmethoxy)-silane (14) (10.0 g) in tetrahydrofuran (300 mL) was cooled to −78° C. with stirring was treated drop-wise with sec-butyllithium (3.0 M in cyclohexane, 37 mL). After 1 hour the reaction mixture was treated drop-wise with a solution of methyl chloroformate (5.2 g) in tetrahydrofuran (30 mL) over 10 mins and stirring was continued at −78° C. for 1 hour. The reaction mixture was then treated with saturated ammonium chloride solution (300 mL) and allowed to warm to ambient temperature. The two layers were separated and the organic phase washed with brine (300 mL), dried and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate/pentane (1:9 by volume) to give compound 15 as a clear oil. stirring The two layers were separated the organic phase washed with brine (300 mL) dried concentrated in vacuo The residue was purified by flash chromatography eluting with ethyl acetate/pentane (1:9 by volume)
Source ID: ord-7d3f5da89a88434d8c988b0287a11a5aConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-6e6bdc4608174b92aee2087e45432ad6Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of triisopropyl-(2-methyl-furan-3-ylmethoxy)-silane (14) (10 g) in tetrahydrofuran (250 mL) was cooled to −78° C. with stirring, and then sec-butyllithium (1.3 M in cyclohexane; 37.25 mL) was added drop-wise over 10 mins. After stirring for 45 mins at −78° C., the cooling bath was removed for a period of 15 mins then re-introduced. A solution of N,N-dimethylformamide (14.4 mL) in tetrahydrofuran (25 mL) was added drop-wise and the resulting reaction mixture was stirred at −78° C. for a further 2 hours. The reaction mixture was allowed to warm to room temperature and then poured into saturated ammonium chloride solution (150 mL). This mixture was extracted with diethyl ether (2×350 mL), and the combined organic extracts were washed with water (500 mL) and brine (500 mL), dried, and concentrated in vacuo to give compound 33 as an amber coloured oil. LC/MS System A: Rt=4.86 mins. After stirring for 45 mins at −78° C. the cooling bath was removed for a period of 15 mins then re-introduced A solution of N,N-dimethylformamide (14.4 mL) in tetrahydrofuran (25 mL) was added drop-wise the resulting reaction mixture was stirred at −78° C. for a further 2 hours This mixture was extracted with diethyl ether (2×350 mL) the combined organic extracts were washed with water (500 mL) and brine (500 mL) dried concentrated in vacuo
Source ID: ord-6dcfcd9382b24fd6926785874ccfa3fbPubChem References
These sources are listed in the compound's public database record.
Request a Quote
Send the required specification, quantity, destination and intended use. The CATO team will review availability and respond.