Aluminium lithium hydride → HCID 58557598, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-tert-butyl 1-methyl 4-ethylcyclopentane-1,3-dicarboxylate (3.88 g, 15.1 mmol, Preparation #11, Step B) in Et2O (150 mL) was cooled to about −40° C. LAH (2 N in THF, 8.32 mL, 16.6 mmol) was added dropwise. The reaction mixture was stirred at about −40° C. for about 1 hour. The reaction mixture was partitioned between saturated aqueous NaHCO3 (50 mL) and EtOAc (3×50 mL). The combined organic extracts were concd under reduced pressure. The crude material was purified by silica gel chromatography eluting with a gradient of 0-100% EtOAc/heptane to give tert-butyl 2-ethyl-4-(hydroxymethyl)cyclopentanecarboxylate (1.00 g, 29%) as a brown oil: LC/MS (Table 1, Method a) Rt=2.37 min; MS m/z: 229 (M+H)+.

Provenance & Evidence