Sodium Hydroxide → HCID 58557273, compound

Participants

Reaction Steps

To a solution of (1S,2R)-ethyl 2-ethyl-4-oxocyclopentanecarboxylate (5 g, 27.1 mmol, Example #22 step B) in THF (100 mL) at about −78° C. was added LAH (2 M in THF, 54.3 mL, 109 mmol). After about 1 h, the reaction mixture was allowed to warm to rt slowly. After about 4 h, water (4.8 mL) followed by aqueous NaOH (15% w/v, 4.8 mL) followed by water (9.6 mL) was added to the reaction mixture. After about 15 h, anhydrous Na2SO4 was added and the slurry was filtered and concd in vacuo to provide crude (3R,4S)-3-ethyl-4-(hydroxymethyl)cyclopentanol (3.9 g, 100%) as an oil which was used without further purification. LC/MS (Table 1, Method a) Rt=2.40 min; MS m/z: 145 (M+H)+.

Provenance & Evidence