Water → HCID 11270256, compound

Participants

Reaction Steps

To a solution of 30 (0.10 g, 0.20 mmol) in CH2Cl2 (5 mL) was added Et3N (0.072 mL, 0.052 g, 0.51 mmol) and propionyl chloride (0.021 mL, 0.021 g, 0.22 mmol). The mixture was stirred at ambient temperature for 1 h, washed with H2O (2×), dried (Na2SO4), concentrated, and dried in vacuo to give an off-white foam. This residue was dissolved in THF (3 mL) and H2O (0.6 mL) and the mixture was stirred at ambient temperature for 5 h. Solvent was evaporated and the residue triturated with hexanes/Et2O (5:1) to provide 7 (0.064 g, 73%) as an off-white solid, mp 155-157° C. 1HNMR (DMSO-d6): δ 0.86 (t, J=7.4 Hz, 3H), 1.05 (t, J=7.4 Hz, 3H), 2.4 (q, J=7.4 Hz, 2H), 2.49 (q, J=7.4 Hz, 2H), 6.51 (d, J=16 Hz, 1H), 6.79 (d, J=8.6 Hz, 2H), 6.85 (d, J=8.6 Hz, 2H), 7.10-7.22 (m, 5H), 7.25 (d, J=8.1 Hz, 2H), 7.59 (d, J=16 Hz, 1H), 7.7 (d, J=8.1 Hz, 2H), 12.33 (br s, 1H); Anal. calculated for C28H26O4.0.25H2O: C, 78.03; H, 6.20; Found: C, 78.02; H, 6.13.

Provenance & Evidence