Sodium Acetate → 2-(5-Phenyl-1-oxopentyl)-2-oxiranecarboxylic acid methyl ester

HRID 2232630

反応式

HRID 2232630 の反応式
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C([O-])(=O)C.[Na+].[CH3:17][O:18][C:19]([C:21]1([CH:24]([OH:35])[CH2:25][CH2:26][CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:23][O:22]1)=[O:20]>C(Cl)Cl.C(OCC)C>[CH3:17][O:18][C:19]([C:21]1([C:24](=[O:35])[CH2:25][CH2:26][CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:23][O:22]1)=[O:20]

参加物

6

反応物 3

HCID 517045Sodium AcetateHCID 143489022-(5-Phenyl-1-hydroxypentyl)-2-oxiranecarboxylic acid methyl esterHCID 178418287HCID 178418287、化合物

生成物 1

HCID 543101722-(5-Phenyl-1-oxopentyl)-2-oxiranecarboxylic acid methyl ester収率 43.3%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

To a suspension of 7.6 g (35.4 mmol) of pyridinium chlorochromate and 2.90 g (35.4 mmol) of anhydrous sodium acetate in 100 ml of methylene chloride is added 1.55 g (5.9 mmol) of 2-(5-phenyl-1-hydroxypentyl)-2-oxiranecarboxylic acid methyl ester. The mixture is stirred at room temperature for 3 hours and then is diluted with ethyl ether. Filtration through Florisil and rotoevaporation gives an oil which is subjected to preparative column chromatography on silica gel (hexane:ethyl ether (3:2)). The appropriate fractions are combined and rotoevaporated to give 670 mg (43.3%) of the title compound: IR (film) 1757, 1723 cm-1 ; NMR (CDCl3) δ 1.65 (4H, m), 2.48-2.65 (4H, mc), 3.06 (1H, d, J=6 Hz), 3.33 (1H, d, J=6 Hz), 3.83 (3H, s), 7.21 (3H, m), 7.30 (2H, m).

後処理

  1. filtrationFiltration through Florisil and rotoevaporation
  2. customgives an oil which

出典と根拠

ORDレコード
ord-748831b21f9840689ab2846c9a8b5d13
出典データセット
uspto-grants-1988_11
特許番号
US04788304

関連ノート

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