Sodium Bicarbonate → HCID 70010871, compound

Participants

Reaction Steps

Dimethoxytrityl chloride (1.21 g, 3.57 mmol) was added to a solution of 8 (1.0 g, 2-94 mmol) in 17 ml of dry pyridine. The solution was stirred at room temperature for 2 h. and then poured into 250 ml of 5% sodium bicarbonate and extracted with 300 ml of ethyl acetate. The extract was dried over sodium sulfate and evaporated. The residue was purified by silica gel chromatography eluting with 50% hexane in ethyl acetate (1% triethylamine). The pure product fractions were pooled and evaporated affording a foam: 1.66 g (85%) yield; TLC (1: 1, ethyl acetate/hexane), Rf=0.50; 1H NMR (CDCl3) 7.62 (1H, s, acetal CH), 7.43 (2H, d, J=8.2 Hz, aromatic), 7.33-6.81 (17H, aromatic), 3.92 (2H, t, J=6.4 Hz, CH2), 3.78 (6H, s, OCH3), 3.17 (1H, dd, J=3.3 and 9.4 Hz, CH), 3.03 (1H, t, J=7.7 Hz, CH), 2.37 (1H, m, CH), 2.10 (6H, s, acetyl), 1.81-1.38 (6H, multiplets, CH2). Anal. Calcd for C38H42O9: C, 71.01; H, 6.59. Found: C, 70.91; H, 6.42.

Provenance & Evidence