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Methyl morpholine oxide → Ethyl 7-(3,5-difluoro-4-triisopropylsilanyloxyphenyl)-6-formylheptanoate

HRID 1921879
ノート
印刷プレビュー

反応式

HRID 1921879 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([F:32])[C:20]=1[O:21][Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[CH2:5][CH:6]([CH2:16][OH:17])[CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].C[N+]1([O-])CCOCC1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[F:32][C:19]1[CH:18]=[C:4]([CH2:5][CH:6]([CH:16]=[O:17])[CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:3]=[C:2]([F:1])[C:20]=1[O:21][Si:22]([CH:26]([CH3:27])[CH3:28])([CH:29]([CH3:31])[CH3:30])[CH:23]([CH3:24])[CH3:25]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 82029Methyl morpholine oxideHCID 57971930Ethyl 6-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)-7-hydroxyheptanoate

生成物 1

HCID 57971915Ethyl 7-(3,5-difluoro-4-triisopropylsilanyloxyphenyl)-6-formylheptanoate

試薬・触媒・溶媒 2

HCID 178419074HCID 178419074、化合物触媒HCID 6344Dichloromethane溶媒

実験手順

1.19 g (2.52 mmol) of ethyl 6-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)-7-hydroxyheptanoate are stirred with 5 g of 4 Å molecular sieves and 442 mg (3.78 mmol) of N-methylmorpholine N-oxide in 50 ml of dichloromethane at room temperature for 10 minutes. 44 mg (0.13 mmol) of tetrapropylammonium perruthenate are added, and the mixture is stirred at room temperature until reaction is complete. The mixture is filtered and the filtrate is washed with water and saturated sodium chloride solution. The organic phase is dried over sodium sulfate and concentrated. The resulting crude product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 3:1). 1.0 g (84% of theory) of the title compound is obtained.

後処理

  1. filtrationThe mixture is filtered
  2. washthe filtrate is washed with water and saturated sodium chloride solution
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe resulting crude product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 3:1)

出典と根拠

ORDレコード
ord-109de2df71b5486db9d65eb79205615a
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08173704B2

反応ノート

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