Diethyl Ether → HCID 57286114、化合物

反応式

[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]=1

参加物

反応物 4

HCID 3283Diethyl Ether

HCID 8058Hexane

HCID 9550Diazomethane

HCID 14507378HCID 14507378、化合物

生成物 1

HCID 57286114HCID 57286114、化合物収率 17%

実験手順

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%):