Hydroxylamine → 3-Octyl acetate

Temperature

0 °C

To a flask containing aminoalcohol A (0.036 g, 0.15 mmol) prepared as in Example 13 was added freshly distilled hexanal (0.30 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 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 95% hexane and 5% ethyl acetate as eluant. The product (+)-3-octyl acetate (0.43 g, 83%) was isolated as a colorless liquid by distillation of the solvent at reduced pressure.

1. customA (0.036 g, 0.15 mmol) prepared as in Example 13
2. customthe reaction was quenched by dropwise addition of half-saturated aqeous ammonium chloride (50 mL)
3. customThe ether layer was separated
4. extractionthe aqueous layer was further extracted with ether (2×50 mL)
5. dry with materialThe combined ether layers were dried over magnesium sulfate whereupon the solvent
6. customwas removed at reduced pressure
7. customThe residue was purified by flash chromatography on 220-400 mesh silica with 95% hexane and 5% ethyl acetate as eluant

ORD record

ord-be3d70efcf9e419a8767a6d669f5d7d0

Source dataset

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06362344B1