Acetic Acid → HCID 18937697, compound

Participants

Reaction Steps

1.5N butyllithium (15.8 ml, 24.88 mmole) was added under the argon atmosphere to a solution of diisopropylamine (3.66 ml, 26.1 mmole) in tetrahydrofuran (50 ml) at -78° C., and the mixture was stirred for 30 minutes. To the reaction mixture were next added a solution of ethyl propiolate (2.20 ml, 21.71 mmole) in tetrahydrofuran (10 ml) and a solution of 4,5-dimethyl-2-nitrobenzaldehyde (2.60 g, 14.51 mmole) in tetrahydrofuran (20 ml) in this sequence, and the reaction mixture was stirred at -78° C. for further 1.5 hours. After a solution of acetic acid (3.2 ml, 53.3 mmole) in tetrahydrofuran (10 ml) followed by water were added, the reaction mixture was extracted with ethyl acetate (300 ml). The organic layer was washed with dilute hydrochloric acid, water, a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous saline in this sequence. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure to give ethyl 4-hydroxy-4(4,5-dimethyl-2-nitrophenyl)-2-butynoate as an oil (4.363 g).

Provenance & Evidence