Imidazole → (S)-2-(tert-Butyldimethylsilyloxy)-g-butyrolactone

Participants

Reaction Steps

Imidazole (241 mg, 3.54 mmol, 2.2 equiv) and tert-butyl-dimethylsilyl chloride (267 mg, 1.77 mmol, 1.1 equiv) are added to a solution of (3S)-dihydro-3-hydroxy-2(3H)-furanone 11 (164 mg, 1.61 mmol) in dimethyl formamide (1.5 ml). The mixture is stirred for 24 h at r.t. Purification of the reaction mixture by flash column chromatography (pentane/diethyl ether 10:1) affords (S)-2-(tert-butyidimethylsilyloxy)-γ-butyrolactone 12 (321 mg, 93%) as a colourless oil. [α]D20=−31.7; [α]54620=−37.4 (c=0.86, CHCl3); 13C-NMR (100 MHz, CDCL3): δ(ppm)=175.8; 68.2; 64.7; 32.3; 25.6; 18.2; −4.8; −5.3

Provenance & Evidence