Triethylamine → HCID 58210349, compound

Participants

Reaction Conditions

Reaction Steps

Acetic acid 5-acetoxy-6-oxo-tetrahydro-pyran-2-ylmethyl ester (2.3) (2.30 g, 10.0 mmol) was dissolved in ethyl acetate (50 mL) and added to the Parr reactor, followed by Pd/C (5%, 0.2 g) and triethylamine (4.3 mL, 30.0 mmol). The mixture was stirred under hydrogen (5×106 Pa) and heated at 50° C. for 1 day. The product was filtered through celite and the solvent removed under vacuum. The crude product was dissolved in CH2Cl2 (200 mL) and washed with water (3×200 mL). The solvent was removed and the resulting product dried under vacuum. The resulting syrup was sublimed under vacuum, at 50° C., affording white crystals (1.20 g, 7.0 mmol, 70%). 1H NMR (400 MHz, CDCl3) δ 5.46 (1H, dd, 3JH—H=10.56 Hz, 3JH—H=8.87 Hz, H-2), 4.60 (1H, m, H-5), 2.36 (1H, m, H-3), 2.20 (3H, s, COCH3), 2.12-2.00 (1H, m, H-4), 2.00-1.88 (1H, m, H-3′), 1.88-1.75 (1H, m, H-4′), 1.42 (3H, d, 3JH—H=6.22 Hz, H-6) ppm. 13C {1H} NMR (125 MHz, CDCl3) δ 169.9, 169.6 (COCH3, C-1), 74.2 (C-5), 66.0 (C-2), 27.8 (C-4), 23.0 (C-3), 21.0 (C-6), 20.8 (COCH3) ppm. m/z (CI-ammonia gas): 190 [M+NH4+]. Anal. Calcd for C8H12O4: C, 55.81; H, 7.02. Found: C, 55.81; H, 7.05.

Provenance & Evidence