Diethyl Ether → HCID 57286114, compound
Reaction equation
[N+](=C)=[N-].[Si:4]([O:21][CH2:22][C@@H:23]1[C@@H:26]([CH2:27][O:28][Si:29]([C:42]([CH3:45])([CH3:44])[CH3:43])([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:25]C1=O)([C:17]([CH3:20])([CH3:19])[CH3:18])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CCCCCC.CC[O:55][CH2:56][CH3:57]>>[Si:4]([O:21][CH2:22][C@@H:23]1[C@@H:26]([CH2:27][O:28][Si:29]([C:42]([CH3:43])([CH3:45])[CH3:44])([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:25][CH2:57][C:56]1=[O:55])([C:17]([CH3:20])([CH3:19])[CH3:18])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1Participants
5
Procedure
A solution of diazomethane (ca. 2 g) in ether (200 ml) was added to (2S,3S)-2,3-bis(t-butyldiphenylsilyloxymethyl)-1-cyclobutanone (12.14 g, 20 mmoles) synthesized according to a method disclosed in literature Y. Ichikawa et al., J. Chem. Soc. Chem. Commun., 1919 (1989)], and the resulting mixture was stirred at room temperature for one week. After distilling off the solvent from the reaction mixture under reduced pressure, the residue was purified by silica gel column chromatography (ethyl ether:n-hexane=1:10, v/v) to obtain (2S,3S)-2,3-bis(t-butyldiphenylsilyloxymethyl)-1-cyclopentanone (2.07 g, Yield 17%):