Cyclohexanemethanol, 4-ethynyl- (9CI) synthesis
- Product Name:Cyclohexanemethanol, 4-ethynyl- (9CI)
- CAS Number:120077-79-4
- Molecular formula:C9H14O
- Molecular Weight:138.21
Yield:120077-79-4 86%
Reaction Conditions:
with potassium carbonate in methanol at 0 - 15; for 12 h;Inert atmosphere;
Steps:
3 Step 3 - (4-Ethynylcyclohexyl)methanol
To a solution of (4-formylcyclohexyl)methyl acetate (5.90 g, 32.0 mmol), potassium carbonate (13.3 g, 96.1 mmol) in methanol (100 mL) was added 1-diazo-1- dimethoxyphosphoryl-propan-2-one (8.00 g, 41.6 mmol, CAS 90965-06-3) at 0 °C. The reaction mixture was stirred at 15 °C for 12 hrs. On completion, the reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (3 X 150 mL). The combined organic layers were washed with brine (2 X 50 mL), dried over anhydrous sodium sulfate, filtered and the concentrated in vacuo. The residue was purified by silica gel chromatography (petroleum ether: ethyl acetate = 8:1 to 4:1) to give the title compound (3.80 g, 86% yield) as a white solid.1H NMR (400MHz, CDCl3) d 3.53 - 3.43 (m, 2H), 2.88 - 2.73 (m, 1H), 2.27 - 2.00 (m, 3H), 1.92 - 1.64 (m, 2H), 1.58 - 0.90 (m, 6H).
References:
WO2020/113233,2020,A1 Location in patent:Paragraph 00962; 003413; 003418-003419
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