Hydroxylamine → Cyclohexanemethanol, alpha-ethyl-, 1-acetate

Participants

Reaction Conditions

Reaction Steps

To a flask containing aminoalcohol A (0.036 g, 0.15 mmol) prepared as in Example 13 was added freshly distilled cyclohexanecarboxaldehyde (0.34 g, 3.0 mmol) and toluene (3.0 mL). The flask was cooled to 0° C. and 1 M diethylzinc in hexane (6.0 mL) was added dropwise. After 3 hours at 0° C., acetic anhydride (1.2 mL, 13 mmol) was added. After 18 hours at 25° C. the mixture was diluted in ether (50 mL) and the reaction was quenched by dropwise addition of half-saturated aqeous ammonium chloride (50 mL). The ether layer was separated and the aqueous layer was further extracted with ether (2×50 mL). The combined ether layers were dried over magnesium sulfate whereupon the solvent was removed at reduced pressure. The residue was purified by flash chromatography on 220-400 mesh silica with 90% hexane and 10% ethyl acetate as eluant. The product (+)-1-cyclohexylpropyl acetate (0.54 g, 97%) was isolated as a colorless liquid by distillation at reduced pressure.

Provenance & Evidence