2-Methyl-3-butyn-2-ol → 1-Methoxy-2,5-dimethylhex-3-yne-2,5-diol

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Reaction Steps

To a solution of anhydrous diethyl ether at 0-5° C. is added ethyl magnesium bromide (37.33 ml, 112 mmol, 3M solution in diethyl ether), then 2-methyl-3-butyn-2-ol (4.70 g, 55.87 mmol) dropwise. The mixture is allowed to warm to room temperature, followed by stirring at this temperature for 30 minutes, then at 40° C. until gas evolution ceases (approximately 1 hour). The viscous mixture is next cooled to room temperature and methoxyacetone (3.78 g, 42.90 mmol) is added dropwise, followed by heating to 40° C. for 1 hour. After cooling to room temperature the suspension is poured into a mixture of ice and saturated aqueous ammonium chloride, and the product is extracted with diethyl ether (2×50 ml) then dichloromethane (2×50 ml, 2×100 ml). The organic extracts are combined, washed with brine, dried over anhydrous magnesium sulfate then concentrated in vacuo to afford 1-methoxy-2,5-dimethylhex-3-yne-2,5-diol (6.98 g) as a clear oil.

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