Diethyl Ether → HCID 57286114, compound

HRID 1492462Notes

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]=1

Participants

Reactant 4

HCID 3283Diethyl Ether

HCID 8058Hexane

HCID 9550Diazomethane

HCID 14507378HCID 14507378, compound

Product 1

HCID 57286114HCID 57286114, compoundYield 17%

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%):

Workup

customsynthesized
distillationAfter distilling off the solvent from the reaction mixture under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl ether

Sources & evidence

ORD record: ord-d8dd825dfb1a445ea68ebb7b21fced95
Source dataset: uspto-grants-1994_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05374625

Reaction notes

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