7-Octynoic acid methyl ester synthesis
- Product Name:7-Octynoic acid methyl ester
- CAS Number:18458-50-9
- Molecular formula:
- Molecular Weight:0
Yield:18458-50-9 434 mg
Reaction Conditions:
in methanol;diethyl ether;hexane; for 23 h;Cooling with ice;
Steps:
Methyl oct-7-ynoate (27)
To an ice-cold solution of 7-octyn-1-ol (26) (474 mg, 3.76 mmol) and DMSO (3.76 mL,52.9 mmol) in CH2Cl2 (9.5 mL) were added Et3N (2.62 mL, 18.8 mmol) and SO3·Py (1.79 g,11.2 mmol). After being stirred for 40 min, the mixture was diluted with brine, and extractedwith hexane three times. The combined extracts were dried over MgSO4 and concentrated toafford a residue, which was used for the next reaction without further purification. To a solution of the above aldehyde in t-BuOH (3 mL) and H2O (3 mL) was added 2-methyl-2-butene (2.00 mL, 18.8 mmol) and NaH2PO4·2H2O (762 mg, 4.88 mmol). Afterbeing stirred for 5 min, NaClO2 (70% content, 1.19 g, 9.24 mmol) was added. The mixturewas stirred at room temperature for 1 h and diluted saturated NH4Cl. The resulting mixturewas extracted with EtOAc three times. The combined extracts were dried over MgSO4 andconcentrated to afford a residue, which was used for the next reaction without furtherpurification.To an ice-cold solution of the above carboxylic acid in Et2O (14.4 mL) and MeOH (9.6mL) was added TMSCHN2 (0.6 M in hexane, 7.5 mL, 4.5 mmol). After being stirred for 23h, the mixture was concentrated. The residue was purified by chromatography on silica gel(CH2Cl2) to give acetylene 27 (434 mg, 75% from 26): colorless oil;
References:
Ogawa, Narihito;Amano, Takahito;Kobayashi, Yuichi [Synlett,2021,vol. 32,# 3,p. 295 - 298] Location in patent:supporting information
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