Imidazole → HCID 11120848, compound

Participants

Reaction Conditions

Reaction Steps

Imidazole (1.230 g, 18.06 mmol, 2.6 equiv) and tert-butyl-dimethylsilyl chloride (1.230 g, 9.03 mmol, 1.3 equiv) are added to a solution of (S)-5-benzyloxy-2-methyl-pentan-1-ol- 4 (1.447 g, 6.95 mmol) in dimethyl formamide (5.5 ml). The mixture is stirred for 1 h at 40° C. Purification of the reaction mixture by flash column chromatography (pentane/diethyl ether 20:1) affords (s)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-4-methyl-pentane 5 (1.985 g, 89%) as a colouriess oil (the reaction mixture is poured directly without aqueous workup onto a flash chromatography column which is pre-wetted with the eluent). 13C-NMR (100 MHz, CDCl3): δ=138.7; 128.3; 127.5; 127.4; 72.8; 70.8; 68.2; 35.6; 29.6; 27.2; 25.9; 18.3; 16.6; −5.4.

Provenance & Evidence