Dimethylformamide → HCID 18936591, compound

Participants

Reaction Steps

Treat a solution of 4-(3,4-dichlorophenyl)-dihydro-5-(hydroxymethyl) 2(3H)-furanone (3.3 g, 12.6 mmol, 3:2 ratio of stereoisomers by NMR) in dry DMF(10 mL) with 3,5-bistrifluoromethylbenzyl bromide (5.9 mL, 32.2 mmol) followed by Ag2O (5.8 g, 25.3 mmol); wrap the vessel in foil and stir for 2.5 d. Apply the crude material to a pad of silica gel (10 cm×4 cm) packed with hexane:EtOAc (1:1), washing the pad with the same solvent until no further product is eluted as shown by TLC; concentrate the resulting filtrate in vacuo to give the crude product as a solid (10 g). Dissolve the crude was dissolved in hexane:EtOAc (4:1) and purify by silica gel chromatography (column: 7.5×19; solvent: hexane:EtOAc, 4:1) to give 3.33 g (6.8 mmol, 54%) of isomer (trans)-[[[(3,5-bis(trifluoromethyl)phenyl]methoxy]methyl]-4-(3,4-dichlorophenyl)-dihydro-2(3H)-furanone and 1.08 g (2.2 mmol, 17%) of the corresponding cis isomer for a total yield of 71%.

Provenance & Evidence