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CC(=O)SC1CCOCC1Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | S-(oxan-4-yl) ethanethioate |
|---|---|
| IUPAC Name | — |
| CAS Number | 203246-70-2 |
| Database ID | 18533108 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
S-(oxan-4-yl) ethanethioate (CAS 203246-70-2) 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 18533108
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-36183d0fa25047069f16c234bc80bdb3Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-71aad5656934420b9ab06be32635ff32Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 153 g (0.96 mol) of thioacetic acid S-(tetrahydro-pyran-4-yl)ester in ethanol (3.5 L) is degassed with nitrogen over 0.5 h and 125 g (2.23 mol) of KOH are added. Then a solution of 250 mL (1.68 mol) of ethyl α-bromoisobutyrate in EtOH (1 L) are added over 0.5 h, during which the temperature increased to 40° C. The reaction is stirred for 18 h at room temperature under a nitrogen atmosphere. The reaction mixture is filtered, the solid is washed with ethanol (0.5 L) and the filtrate is concentrated under reduced pressure. The crude material is dryloaded onto silica and purified by dry-flash column chromatography (silica, eluent: n-heptanes, 2-10% ethyl acetate) to afford 158 g of 2-methyl-2-(tetrahydro-pyran-4-ylsulfanyl)-propionic acid ethyl ester as an orange-brown oil. Yield: 71%; ES-MS: m/z 233 [M+H] The reaction mixture is filtered the solid is washed with ethanol (0.5 L) the filtrate is concentrated under reduced pressure purified by dry-flash column chromatography (silica, eluent: n-heptanes, 2-10% ethyl acetate)
Source ID: ord-b1821256fe614b75b8dc7bf4229ca1c3Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 300 g (1.175 mol) of toluene-4-sulfonic acid tetrahydropyran-4-yl ester in DMF (3 L) are added 268 g (2.35 mol) potassium thioacetate, followed by a catalytic amount of NaI (0.12 g, 10 mol %) at room temperature. After complete addition, the reaction is heated to 50° C. for 20 h. The reaction mixture is partitioned between TBME (3 L) and water (3 L), the aqueous layer is extracted with TBME (2 L), then saturated with NaCl and extracted again with TBME (2×2 L). The combined organic extracts are dried over Na2SO4, filtered and the solvent is removed under reduced pressure to afford 153 g of thioacetic acid S-(tetrahydro-pyran-4-yl)ester. Yield: 81%; ES-MS: m/z 161 [M+H]. After complete addition The reaction mixture is partitioned between TBME (3 L) and water (3 L) the aqueous layer is extracted with TBME (2 L) saturated with NaCl and extracted again with TBME (2×2 L) The combined organic extracts are dried over Na2SO4 filtered the solvent is removed under reduced pressure
Source ID: ord-8d1f75d8a7c44ba88b203fe57d0003a6Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 153 g (0.96 mol) of thioacetic acid S-(tetrahydro-pyran-4-yl)ester in ethanol (3.5 L) is degassed with nitrogen over 0.5 h and 125 g (2.23 mol) of KOH are added. Then a solution of 250 mL (1.68 mol) of ethyl α-bromoisobutyrate in EtOH (1 L) are added over 0.5 h, during which the temperature is increased to 40° C. The reaction is stirred for 18 h at room temperature under a nitrogen atmosphere. The reaction mixture is filtered, the solid is washed with ethanol (0.5 L) and the filtrate is concentrated under reduced pressure. The crude material is dryloaded onto silica and purified by dry-flash column chromatography (silica, eluent: n-heptanes, 2-10% ethyl acetate) to afford 158 g of 2-methyl-2-(tetrahydro-pyran-4-ylsulfanyl)-propionic acid ethyl ester as an orange-brown oil. Yield: 71%; ES-MS: m/z 233 [M+H]; 1H-NMR The reaction mixture is filtered the solid is washed with ethanol (0.5 L) the filtrate is concentrated under reduced pressure purified by dry-flash column chromatography (silica, eluent: n-heptanes, 2-10% ethyl acetate)
Source ID: ord-183e5671a3df44f599e43512206e1eceConditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 300 g (1.175 mol) of toluene-4-sulfonic acid tetrahydro-pyran-4-yl ester in DMF (3 L) are added 268 g (2.35 mol) potassium thioacetate, followed by a catalytic amount of NaI (0.12 g, 10 mol %) at room temperature. After complete addition, the reaction is heated to 50° C. for 20 h. The reaction mixture is partitioned between TBME (3 L) and water (3 L), the aqueous layer is extracted with TBME (2 L), then saturated with NaCl and extracted again with TBME (2×2 L). The combined organic extracts are dried over Na2SO4, filtered and the solvent is removed under reduced pressure to afford 153 g of thioacetic acid S-(tetrahydro-pyran-4-yl)ester. Yield: 81%; ES-MS: m/z 161 [M+H]; 1H-NMR (250 MHz, CHLOROFORM-d) δ ppm 1.47-1.98 (4 H, m), 2.30 (3 H, s), 3.41-3.74 (3 H, m), 3.88 (2 H, dt, J=11.76, 3.86 Hz) After complete addition The reaction mixture is partitioned between TBME (3 L) and water (3 L) the aqueous layer is extracted with TBME (2 L) saturated with NaCl and extracted again with TBME (2×2 L) The combined organic extracts are dried over Na2SO4 filtered the solvent is removed under reduced pressure
Source ID: ord-62c0de0ff38c4677afb6738f950145d4Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 300 g (1.175 mol) of toluene-4-sulfonic acid tetrahydro-pyran-4-yl ester in DMF (3 L) are added 268 g (2.35 mol) potassium thioacetate, followed by a catalytic amount of NaI (0.12 g, 10 mol %) at room temperature. After complete addition, the reaction is heated to 50° C. for 20 h. The reaction mixture is partitioned between TBME (3 L) and water (3 L), the aqueous layer is extracted with TBME (2 L), then saturated with NaCl and extracted again with TBME (2×2 L). The combined organic extracts are dried over Na2SO4, filtered and the solvent is removed under reduced pressure to afford 153 g of thioacetic acid S-(tetrahydro-pyran-4-yl)ester. Yield: 81%; ES-MS: m/z 161 [M+H]; 1H-NMR (250 MHz, CHLOROFORM-d) δ ppm 1.47-1.98 (4 H, m), 2.30 (3 H, s), 3.41-3.74 (3 H, m), 3.88 (2 H, dt, J=11.76, 3.86 Hz) After complete addition The reaction mixture is partitioned between TBME (3 L) and water (3 L) the aqueous layer is extracted with TBME (2 L) saturated with NaCl and extracted again with TBME (2×2 L) The combined organic extracts are dried over Na2SO4 filtered the solvent is removed under reduced pressure
Source ID: ord-62c0de0ff38c4677afb6738f950145d4Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 153 g (0.96 mol) of thioacetic acid S-(tetrahydro-pyran-4-yl)ester in ethanol (3.5 L) is degassed with nitrogen over 0.5 h and 125 g (2.23 mol) of KOH are added. Then a solution of 250 mL (1.68 mol) of ethyl α-bromoisobutyrate in EtOH (1 L) are added over 0.5 h, during which the temperature is increased to 40° C. The reaction is stirred for 18 h at room temperature under a nitrogen atmosphere. The reaction mixture is filtered, the solid is washed with ethanol (0.5 L) and the filtrate is concentrated under reduced pressure. The crude material is dryloaded onto silica and purified by dry-flash column chromatography (silica, eluent: n-heptanes, 2-10% ethyl acetate) to afford 158 g of 2-methyl-2-(tetrahydro-pyran-4-ylsulfanyl)-propionic acid ethyl ester as an orange-brown oil. Yield: 71%; ES-MS: m/z 233 [M+H] The reaction mixture is filtered the solid is washed with ethanol (0.5 L) the filtrate is concentrated under reduced pressure purified by dry-flash column chromatography (silica, eluent: n-heptanes, 2-10% ethyl acetate)
Source ID: ord-17ff8094abbd4a95ae56354ce95e48cbConditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 153 g (0.96 mol) of thioacetic acid S-(tetrahydro-pyran-4-yl)ester in ethanol (3.5 L) is degassed with nitrogen over 0.5 h and 125 g (2.23 mol) of KOH are added. Then a solution of 250 mL (1.68 mol) of ethyl α-bromoisobutyrate in EtOH (1 L) are added over 0.5 h, during which the temperature is increased to 40° C. The reaction is stirred for 18 h at room temperature under a nitrogen atmosphere. The reaction mixture is filtered, the solid is washed with ethanol (0.5 L) and the filtrate is concentrated under reduced pressure. The crude material is dryloaded onto silica and purified by dry-flash column chromatography (silica, eluent: n-heptanes, 2-10% ethyl acetate) to afford 158 g of 2-methyl-2-(tetrahydro-pyran-4-ylsulfanyl)-propionic acid ethyl ester as an orange-brown oil. Yield: 71%; ES-MS: m/z 233 [M+H] The reaction mixture is filtered the solid is washed with ethanol (0.5 L) the filtrate is concentrated under reduced pressure purified by dry-flash column chromatography (silica, eluent: n-heptanes, 2-10% ethyl acetate)
Source ID: ord-17ff8094abbd4a95ae56354ce95e48cbConditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 300 g (1.175 mol) of toluene-4-sulfonic acid tetrahydropyran-4-yl ester in DMF (3 L) are added 268 g (2.35 mol) potassium thioacetate, followed by a catalytic amount of NaI (0.12 g, 10 mol %) at room temperature. After complete addition, the reaction is heated to 50° C. for 20 h. The reaction mixture is partitioned between TBME (3 L) and water (3 L), the aqueous layer is extracted with TBME (2 L), then saturated with NaCl and extracted again with TBME (2×2 L). The combined organic extracts are dried over Na2SO4, filtered and the solvent is removed under reduced pressure to afford 153 g of thioacetic acid S-(tetrahydro-pyran-4-yl)ester. Yield: 81%; ES-MS: m/z 161 [M+H]. After complete addition The reaction mixture is partitioned between TBME (3 L) and water (3 L) the aqueous layer is extracted with TBME (2 L) saturated with NaCl and extracted again with TBME (2×2 L) The combined organic extracts are dried over Na2SO4 filtered the solvent is removed under reduced pressure
Source ID: ord-fed09d7da59d43999710ee5afc30b168Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 153 g (0.96 mol) of thioacetic acid S-(tetrahydro-pyran-4-yl) ester in EtOH (3.5 L) is degassed with nitrogen over 0.5 h and 125 g (2.23 mol) of KOH are added. Then a solution of 250 mL (1.68 mol) of ethyl α-bromoisobutyrate in EtOH (1 L) are added over 0.5 h, during which the temperature increased to 40° C. The reaction is stirred for 18 h at RT under a nitrogen atmosphere. The reaction mixture is filtered, the solid is washed with EtOH (0.5 L) and the filtrate is concentrated under reduced pressure. The crude material is dryloaded onto silica and purified by dry-flash column chromatography (silica, eluent: nheptanes, 2-10% EE) to afford 158 g of 2-methyl-2-(tetrahydro-pyran-4-ylsulfanyl)-propionic acid ethyl ester. Yield: 71%; ESI-MS: 233 [M+H]+ The reaction mixture is filtered the solid is washed with EtOH (0.5 L) the filtrate is concentrated under reduced pressure purified by dry-flash column chromatography (silica, eluent: nheptanes, 2-10% EE)
Source ID: ord-03ba5336fd2d48d5ae590f54cfa3d1f4Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To 300 g (1.175 mol) of toluene-4-sulfonic acid tetrahydropyran-4-yl ester in DMF (3 L) are added 268 g (2.35 mol) potassium thioacetate, followed by a catalytic amount of NaI (0.12 g, 10 mol %) at RT. After complete addition, the reaction is heated to 50° C. for 20 h. The reaction mixture is partitioned between TBME (3 L) and water (3 L), the aq. layer is extracted with TBME (2 L), then saturated with NaCl and extracted again with TBME (2×2 L). The combined organic extracts are dried over Na2SO4, filtered and the solvent is removed under reduced pressure to afford 153 g of thioacetic acid S-(tetrahydro-pyran-4-yl) ester. Yield: 81%; ESI-MS: 161 [M+H]+ After complete addition The reaction mixture is partitioned between TBME (3 L) and water (3 L) the aq. layer is extracted with TBME (2 L) saturated with NaCl and extracted again with TBME (2×2 L) The combined organic extracts are dried over Na2SO4 filtered the solvent is removed under reduced pressure
Source ID: ord-b6c0326b5db24e7cb87ed512d00feaf8PubChem References
These sources are listed in the compound's public database record.
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