Chloroform → HCID 19389477, compound

Participants

Reaction Conditions

Reaction Steps

3-Acetoxy-6-acetoxymethyl-pyran-2-one (2.2) (4.80 g, 21.2 mmol) was dissolved in ethyl acetate (50 mL) and added to the Parr reactor, followed by Pd/C (5%, 0.2 g). The mixture was stirred under hydrogen (5×106 Pa) and heated to 75° C. for 4 hours. The product was filtered through celite and the solvent removed under vacuum. A colourless syrup was obtained (4.83 g, 21.0 mmol, 99%). 1H NMR (400 MHz, CDCl3) δ 5.45 (1H, dd, 3JH—H=17.08 Hz, 3JH—H=8.55 Hz, H-2), 4.65 (1H, m, H-5), 4.26 (1 H, dd, 2JH—H=12.13 Hz, 3JH—H=3.54 Hz, H-6), 4.18 (1 H, dd, 2JH—H=12.16, 3JH—H=6.32 Hz, H-6′), 2.36 (1H, m, H-3), 2.19 (3H, s, COCH3), 2.11 (3H, s, COCH3), 2.07-1.88 (3H, m, H-3′, H-4, H-4′) ppm. 13C{1H} NMR (125 MHz, CDCl3) δ 170.6, 169.8, 168.6 (2×COCH3, C-1), 74.9 (C-5), 65.9 (C-2), 64.9 (C-6), 22.7, 22.4 (C-3, C-4), 20.7 (2×COCH3) ppm. CI (NH4+): 248 (100%), 306 (30%), 478 (20%). m/z (CI-ammonia gas): 248 [M+NH4+]. [α]D=0° (CHCl3, 10 mg/mL). Anal. Calcd for C10H14O6: C, 52.17; H, 6.13. Found: C, 52.11; H, 6.17.

Provenance & Evidence