Hydroxylamine → 2-METHYL-3-PENTYL ACETATE

Participants

Reaction Steps

A vial was charged with aminoalcohol 1 (0.0067 g, 0.023 mmol) prepared as in Example 1. To the vial was added 1.45 mL of a stock solution containing freshly distilled isobutyraldehyde (0.22 g), chlorobenzene internal standard (0.22 g), 1 M diethylzinc in hexane (6.0 mL), and toluene (3.0 mL). After 48 h, acetic anhydride (0.200 mL) was added. After an additional 72 h, a sample of the solution was analyzed by gas chromatography at 70° C. on a Cyclodex B stationary phase. The product 3-acetoxy-2-methylpentane was formed in 100% yield and 97% enantiomeric excess. The identity and yield of the product was established by comparison with an authentic sample prepared by treatment of racemic 2,2-dimethyl-3-pentanol with acetic anhydride.

Provenance & Evidence