Acetyl chloride → HCID 45082326, compound

Participants

Reaction Steps

Acetyl chloride (460 mL, 6470 mmol) was added via addition funnel to methanol (1080 mL) at 0° C. A solution of 1 (18.3 g, 71.8 mmol) in methanol (10 mL) was added and the reaction mixture refluxed for 3 hours. Evaporation of the volatiles in vacuo produced a white solid which was dissolved in dioxane (150 mL) and H2O (50 mL). NaHCO3 (12.1 g, 144 mmol) and benzyl chloroformate (20.5 mL, 144 mmol) were added, and the reaction mixture was stirred overnight. The reaction mixture was extracted with EtOAc (3×), and the combined organic phases were washed with brine, dried over MgSO4, filtered and concentrated. Column chromatography (SiO2, EtOAc—hexane gradient elution) afforded 2 (12.25 g, 58%) as a colorless oil: [α]RTD−0.4° (c2.1, CHCl3); 1H NMR (300 MHz, CDCl3) δ7.37-7.29 (m, 5H), 5.79 (br s, 1H), 5.68-5.52 (m, 1H), 5.15-5.01 (m, 4H), 4.18-4.07 (m, 1H), 3.88-3.76 (m, 1H), 3.75 (s, 3H), 3.51 (br s, 1H), 2.78 (dd, J=13.8, 7.8 Hz, 1H), 2.52 (dd, J=14.1, 7.2 Hz, 1H); 13C NMR (75 MHz, CDCl3) δ172.25, 155.24, 135.95, 131.02, 128.36, 128.04, 127.90, 119.91, 66.69, 65.08, 64.93, 52.73, 36.73; IR (film) νmax 3407, 1724 cm−1.

Provenance & Evidence