Nitrogen → HCID 67046197, compound

Participants

Reaction Steps

R)-3-Cyclopropyl-3-hydroxy-1-propene (150 mg, 1.53 mmole) was dissolved in anhydrous CH2Cl2 (5 ml) and the mixture was stirred at 0° C./N2. Then Et3N (248 mg, 341 μL, 2.45 mmole) and t-butyl(dimethyl)silyl-trifluoromethane-sulfonate (525 mg, 456 mL, 1.99 mmol) were added. After 1 h 10% aq. KHCO3 (5 mL) was added and the mixture was stirred at room temp. for 1 h. CH2Cl2 (5 mL) was added, the phases were separated, the organic phase was washed with 10% aq. KHCO3 solution (3×8 mL). The combined organic phases were dried over anhydrous K2CO3, filtered and concentrated in vacuo. The crude product was purified on the column with silica gel (230-400 mesh, 10 g, hexane). After drying the product under vacuum (0° C., 10 mm Hg), (3R)-3-t-butyl(dimethyl)silyloxy-3-cyclopropyl-1-propene as a colourless oil (250 mg, 77%) was obtained; C12H24OSi; E1 MS m/z 212 (M+, 3%); [α]D=+8.0° (20° C., c=1, CHCl3); 1H-NMR (200 MHz, CDCl3) δ 5.89 (1H, ddd: 16.9, 10.4, 5.6 Hz), 5.16 (1H, ddd: 17.2,2.0, 1.2 Hz), 5.02 (1H, ddd: 10.4, 1.8, 1.2 Hz), 3.65 (1H, bt: 6.3 Hz), 0.90 (9H, s), 0.89 (1H, m), 0.43 (2H, m), 0.30 (1H, m), 0.26 (1H, m), 0.05 (3H, s), 0.03 (3H, s) ppm.

Provenance & Evidence