Hydroxylamine → HCID 22625130, compound

Participants

Reaction Steps

To a roundbottom flask containing aminoalcohol 1 (0.05 g, 0.17 mmol) prepared as in Example 1 and 1 M diethylzinc in hexane (6.0 mL) was added dropwise a solution of 3-thiophenecarboxaldehyde (0.32 g, 3.0 mmol) in toluene (3.0 mL). After 3 days at room temperature, acetic anhydride (1.2 mL, 13 mmol) was added. After 2 additional days, the mixture was diluted in ether (50 mL) and the reaction was quenched by dropwise addition of half-saturated aqueous 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-(3-thienyl)propyl acetate (0.45 g, 81%) was isolated as a colorless liquid by distillation at reduced pressure. Anal. for C9H12O2S. Calcd: C, 58.67; H, 6.56; found: C, 58.80; H, 6.75. 1H NMR (CDCl3/TMS): δ 1.86 (t, 3 H, J=7), 1.80-1.88 (m, 1 H), 1.88-1.97 (m, 1 H), 2.04 (s, 3 H), 5.81 (t, 1 H, J=7), 7.05 (m 1 H), 7.20 (m, 1 H), 7.26 (m, 1 H). 13C NMR (CDCl3/TMS): δ 9.85, 21.22, 28.58, 73.10, 122.34, 125.87, 126.04, 141.46, 170.39. [α]D25=+131.7, c=2.06 g/100 mL chloroform. Chiral capillary gas chromatographic analysis at 120° C. on Cyclodex B stationary phase (J & W Scientific) indicated that the enantiomeric excess of the product was 96%.

Provenance & Evidence