Chloromethyl Methyl Ether → HCID 68744172, compound

Participants

Reaction Conditions

Reaction Steps

A solution of diisopropylamine (19.0 mL) in THF was treated dropwise with butyl lithium (82.5 mL of 1.6M solution in hexanes) at −10° C. Next the reaction mixture was cooled to −78° C. and treated dropwise with 2-(cyclohexyl-methyl)-γ-butyrolactone (18.0 mL) keeping the speed of the addition at such a rate that the temperature of the mixture remained below −60° C. After completion of the addition, the mixture was stirred for 4.5 h at −78° C., then warmed-up to −40° C. and treated dropwise at this temperature with chloromethyl methyl ether (10.8 mL). After that, the mixture was allowed to slowly warm-up to room temperature and stirred at this temperature for 60 h. The solvents were removed in vacuum and the residue was redissolved in dichloromethane, then washed with a saturated aqueous solution of ammonium chloride, dried over magnesium sulfate, filtered, concentrated on a rotary evaporator and finally distilled in vacuum to give 5.90 g (25%) of the title compound.

Provenance & Evidence