Ethylene Glycol → HCID 58554741, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 22 (1.2 g, 3.10 mmol) in CH2Cl2 (20 mL) were added DCC (0.703 g, 3.40 mmol) and catalytic amount of DMAP (0.057 g, 0.46 mmol) under nitrogen atmosphere. The reaction mixture was cooled to 0° C. and ethylene glycol (0.770 g, 0.680 mL, 12.4 mmol) in CH2Cl2 (5 mL) was added dropwise. The reaction mixture was allowed to warm up to room temperature and stirred for 12 h. The solid DCU was removed by filtration and the filtrate was evaporated under reduced pressure. The crude residue obtained was dissolved in CH2Cl2 (100 mL), washed with water (40 mL×2), brine (40 mL×2), dried over Na2SO4, filtrated and then concentrated to get a yellow residue. A flash chromatography using CH3OH:CH2Cl2 (1:99) as eluent afforded (S)-1-benzyl 5-(2-hydroxyethyl) 2-(9H-carbazol-9-yl)pentanedioate 23 (0.950 g, 71%) as a yellow gummy liquid.

Provenance & Evidence