(2S,3S)-4-benzyloxy-2,3-epoxy-1-butanol tert-butyldimethylsilyl ether → 3-Tolylmethyl-2-butanol
Reaction equation
[Si](O[CH2:9][C@@H:10]1[O:21][C@H:11]1[CH2:12]OCC1C=CC=CC=1)(C(C)(C)C)(C)C.[C:22]1([CH3:31])[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][Mg]Br)[CH:23]=1>>[C:22]1([CH3:31])[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][CH2:12][CH:11]([OH:21])[CH2:10][CH3:9])[CH:23]=1Participants
3
Procedure
325 mg of (2S,3S)-4-benzyloxy-2,3-epoxy-1-butanol tert-butyldimethylsilyl ether obtained in Example 53. was subjected to Grignard reaction in the same manner as in Example 53 by using 3-tolylmethyl magnesium bromide (0.8M diethyl ether solution). The product was purificated by silica gel column chromatography to obtain 210 mg of (2R,3R)-4-benzyloxy-1-tert-butyldimethylsilyloxy-3-(3-tolylmethyl-2-butanol as colorless oily substance.
Workup
- customwas subjected to Grignard reaction in the same manner as in Example 53