No renderable structure data available
COC(=O)CCCC#CCOChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | methyl 7-hydroxyhept-5-ynoate |
|---|---|
| IUPAC Name | — |
| CAS Number | 50781-91-4 |
| Database ID | 11789443 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
methyl 7-hydroxyhept-5-ynoate (CAS 50781-91-4) 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 11789443
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-eafcfe3bade948218b20aec58bf8659eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 30 (1.347 g, 8.6 mmol) in 5 mL dichloromethane was added to a mixture of triphenylphosphine (2.725 g, 10.4 mmol), imidazole (726 mg, 10.7 mmol), and iodine (2.602 g, 10.3 mmol) in 34 mL dichloromethane, rinsing with 5 mL dichloromethane. After 40 min., the dichloromethane was evaporated in vacuo to a few mL's and the resulting mixture filtered through basic alumina, washing with 10% ethyl acetate/hexanes. Purification by flash chromatography on silica gel (10% ethyl acetate/hexanes) gave 1.878 g (7.1 mmol, 83%) of the propargyl iodide. rinsing with 5 mL dichloromethane the dichloromethane was evaporated in vacuo to a few mL's the resulting mixture filtered through basic alumina washing with 10% ethyl acetate/hexanes Purification by flash chromatography on silica gel (10% ethyl acetate/hexanes)
Source ID: ord-6b24386f1c4a4331914ef83e289d962fConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The crude acid 29 (6.333 g) was treated with a 1% solution of acetyl chloride in methanol (60 mL). After 16 h, sodium bicarbonate (1.966 g, 23.4 mmol) was added. The mixture was dried (MgSO4), filtered through celite and evaporated in vacuo. Purification by flash chromatography on silica gel (30-40% ethyl acetate/hexanes) gave 7-Hydroxy-hept-5-ynoic acid methyl ester 30 (3.022 g, 19.3 mmol, 92% from 7-(tert-Butyl-dimethyl-silanyloxy)-hept-2-yn-1-ol 27). The mixture was dried (MgSO4) filtered through celite evaporated in vacuo Purification by flash chromatography on silica gel (30-40% ethyl acetate/hexanes)
Source ID: ord-0c00cfeee375472f841eceb70c1b5530Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of (30) (1.347 g, 8.6 mmol) in 5 mL dichloromethane was added to a mixture of triphenylphosphine (2.725 g, 10.4 mmol), imidazole (726 mg, 10.7 mmol), and iodine (2.602 g, 10.3 mmol) in 34 mL dichloromethane, rinsing with 5 mL dichloromethane. After 40 minutes, the dichloromethane was evaporated in vacuo to about 2 mL and the resulting mixture filtered through basic alumina, washing with 10% ethyl acetate/hexanes. Purification by flash chromatography on silica gel (10% ethyl acetate/hexanes) gave 1.878 g (7.1 mmol, 83%) of the propargyl iodide. rinsing with 5 mL dichloromethane the dichloromethane was evaporated in vacuo to about 2 mL the resulting mixture filtered through basic alumina washing with 10% ethyl acetate/hexanes Purification by flash chromatography on silica gel (10% ethyl acetate/hexanes)
Source ID: ord-05501bd9f7d0469489ae764d524d12f8Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of (30) (1.347 g, 8.6 mmol) in 5 mL dichloromethane was added to a mixture of triphenylphosphine (2.725 g, 10.4 mmol), imidazole (726 mg, 10.7 mmol), and iodine (2.602 g, 10.3 mmol) in 34 mL dichloromethane, rinsing with 5 mL dichloromethane. After 40 minutes, the dichloromethane was evaporated in vacuo to about 2 mL and the resulting mixture filtered through basic alumina, washing with 10% ethyl acetate/hexanes. Purification by flash chromatography on silica gel (10% ethyl acetate/hexanes) gave 1.878 g (7.1 mmol, 83%) of the propargyl iodide. rinsing with 5 mL dichloromethane the dichloromethane was evaporated in vacuo to about 2 mL the resulting mixture filtered through basic alumina washing with 10% ethyl acetate/hexanes Purification by flash chromatography on silica gel (10% ethyl acetate/hexanes)
Source ID: ord-dbd2f8efefd5423296d6b7c00acb1046Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of (30) (1.347 g, 8.6 mmol) in 5 mL dichloromethane was added to a mixture of triphenylphosphine (2.725 g, 10.4 mmol), imidazole (726 mg, 10.7 mmol), and iodine (2.602 g, 10.3 mmol) in 34 mL dichloromethane, rinsing with 5 mL dichloromethane. After 40 minutes, the dichloromethane was evaporated in vacuo to about 2 mL and the resulting mixture filtered through basic alumina, washing with 10% ethyl acetate/hexanes. Purification by flash chromatography on silica gel (10% ethyl acetate/hexanes) gave 1.878 g (7.1 mmol, 83%) of the propargyl iodide. rinsing with 5 mL dichloromethane the dichloromethane was evaporated in vacuo to about 2 mL the resulting mixture filtered through basic alumina washing with 10% ethyl acetate/hexanes Purification by flash chromatography on silica gel (10% ethyl acetate/hexanes)
Source ID: ord-4973b58eb32f4748aeaeb85260a0d9f7Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of (30) (1.347 g, 8.6 mmol) in 5 mL dichloromethane was added to a mixture of triphenylphosphine (2.725 g, 10.4 mmol), imidazole (726 mg, 10.7 mmol), and iodine (2.602 g, 10.3 mmol) in 34 mL dichloromethane, rinsing with 5 mL dichloromethane. After 40 minutes, the dichloromethane was evaporated in vacuo to about 2 mL and the resulting mixture filtered through basic alumina, washing with 10% ethyl acetate/hexanes. Purification by flash chromatography on silica gel (10% ethyl acetate/hexanes) gave 1.878 g (7.1 mmol, 83%) of the propargyl iodide. rinsing with 5 mL dichloromethane the dichloromethane was evaporated in vacuo to about 2 mL the resulting mixture filtered through basic alumina washing with 10% ethyl acetate/hexanes Purification by flash chromatography on silica gel (10% ethyl acetate/hexanes)
Source ID: ord-277c602f14144300b2842281ad12270aConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-eafcfe3bade948218b20aec58bf8659eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 30 (1.347 g, 8.6 mmol) in 5 mL dichloromethane was added to a mixture of triphenylphosphine (2.725 g, 10.4 mmol), imidazole (726 mg, 10.7 mmol), and iodine (2.602 g, 10.3 mmol) in 34 mL dichloromethane, rinsing with 5 mL dichloromethane. After 40 min., the dichloromethane was evaporated in vacuo to a few mL's and the resulting mixture filtered through basic alumina, washing with 10% ethyl acetate/hexanes. Purification by flash chromatography on silica gel (10% ethyl acetate/hexanes) gave 1.878 g (7.1 mmol, 83%) of the propargyl iodide. rinsing with 5 mL dichloromethane the dichloromethane was evaporated in vacuo to a few mL's the resulting mixture filtered through basic alumina washing with 10% ethyl acetate/hexanes Purification by flash chromatography on silica gel (10% ethyl acetate/hexanes)
Source ID: ord-6b24386f1c4a4331914ef83e289d962fConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The crude acid 29 (6.333 g) was treated with a 1% solution of acetyl chloride in methanol (60 mL). After 16 h, sodium bicarbonate (1.966 g, 23.4 mmol) was added. The mixture was dried (MgSO4), filtered through celite and evaporated in vacuo. Purification by flash chromatography on silica gel (30-40% ethyl acetate/hexanes) gave 7-Hydroxy-hept-5-ynoic acid methyl ester 30 (3.022 g, 19.3 mmol, 92% from 7-(tert-Butyl-dimethyl-silanyloxy)-hept-2-yn-1-ol 27). The mixture was dried (MgSO4) filtered through celite evaporated in vacuo Purification by flash chromatography on silica gel (30-40% ethyl acetate/hexanes)
Source ID: ord-0c00cfeee375472f841eceb70c1b5530Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The crude acid 29 (6.333 g) was treated with a 1% solution of acetyl chloride in methanol (60 mL). After 16 h, sodium bicarbonate (1.966 g, 23.4 mmol) was added. The mixture was dried (MgSO4), filtered through celite and evaporated in vacuo. Purification by flash chromatography on silica gel (30-40% ethyl acetate/hexanes) gave 7-Hydroxy-hept-5-ynoic acid methyl ester 30 (3.022 g, 19.3 mmol, 92% from 7-(tert-Butyl-dimethyl-silanyloxy)-hept-2-yn-1-ol 27). The mixture was dried (MgSO4) filtered through celite evaporated in vacuo Purification by flash chromatography on silica gel (30-40% ethyl acetate/hexanes)
Source ID: ord-0c00cfeee375472f841eceb70c1b5530Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of (30) (1.347 g, 8.6 mmol) in 5 mL dichloromethane was added to a mixture of triphenylphosphine (2.725 g, 10.4 mmol), imidazole (726 mg, 10.7 mmol), and iodine (2.602 g, 10.3 mmol) in 34 mL dichloromethane, rinsing with 5 mL dichloromethane. After 40 minutes, the dichloromethane was evaporated in vacuo to about 2 mL and the resulting mixture filtered through basic alumina, washing with 10% ethyl acetate/hexanes. Purification by flash chromatography on silica gel (10% ethyl acetate/hexanes) gave 1.878 g (7.1 mmol, 83%) of the propargyl iodide. rinsing with 5 mL dichloromethane the dichloromethane was evaporated in vacuo to about 2 mL the resulting mixture filtered through basic alumina washing with 10% ethyl acetate/hexanes Purification by flash chromatography on silica gel (10% ethyl acetate/hexanes)
Source ID: ord-05501bd9f7d0469489ae764d524d12f8PubChem References
These sources are listed in the compound's public database record.
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