Tetrahydrofuran → HCID 15218718, compound

Participants

Reaction Steps

Under nitrogen flow, a solution of methyl propiolate (compound 6) (1.68 g; 20.0 mmoles) in 4 ml of dry THF was added dropwise to a solution of 20.0 ml (20.0 mmoles) of 1M LiN(TMS)2 -THF in 40 ml of dry THF at -78° C. After completion of the addition, the reaction solution was stirred for 1 hour, and a solution of 2.24 g (20.0 mmoles) of cyclohexanecarboxyaldehyde (compound 9k) in 5 ml of dry THF was added dropwise thereto. The mixture was stirred for additional 1 hour, a saturated aqueous ammonium chloride was added to the reaction solution and the mixture was extracted with ethyl acetate. The extract was washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give a crude product of the desired alcohol 10k as an oil. This was used in the next reaction without further purification.

Provenance & Evidence