Carbon Dioxide → alpha-Methoxycarbonyl-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acetic acid

Participants

Reaction Conditions

Reaction Steps

2.1 ml (14.6 mmol) of diisopropylamine and 80 ml of TEP were introduced into a three-necked flask under a nitrogen stream. At -78° C., 5.8 ml (14.6 mmol) of n-butyllithium (2.5M) were added dropwise, the mixture was stirred for 30 minutes, then a solution of 3.2 g (12.2 mmol) of methyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylacetate dissolved in 80 ml of THF was added dropwise and the mixture was stirred for one hour. While maintained at -78° C., CO2 was introduced for 30 minutes and then the temperature was permitted to increase to -40° C. and the reaction medium was poured into a 5N hydrochloric acid solution. The mixture was extracted with ethyl acetate, the organic phase decanted, dried over magnesium sulfate and evaporated. 3.7 g (100%) of expected acid were recovered in the form of a slightly yellow oil.

Provenance & Evidence