Water → Tert-butyl 3-(4-formylphenyl)-2,2-dimethylpropionate

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Reaction Conditions

Reaction Steps

At −75° C., 13.5 ml (22.98 mmol) of a 1.7 M tert-butyllithium solution in pentane are slowly added to a solution of 6.00 g (19.16 mmol) of tert-butyl 3-(4-bromophenyl)-2,2-dimethylpropionate (Example I-2) in 80 ml of tetrahydrofuran, the temperature being kept below −60° C. The mixture is stirred for 15 min, and 1.82 g (24.90 mmol) of N,N-dimethylformamide are then added and the mixture is stirred at −75° C. for a further 4 h. The mixture is slowly warmed to −20° C. and, with vigorous stirring, admixed with 20 ml of water, and then warmed to room temperature. The aqueous phase is extracted 3× with diethyl ether and the combined organic phases are dried over sodium sulfphate/sodium carbonate and freed from the solvent under reduced pressure. Distillation of the residue under oilpump vacuum gives 2.54 g (51%) of tert-butyl 3-(4-formylphenyl)-2,2-dimethylpropionate.

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