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Dichloromethane → {[4-(Benzyloxy)cyclohex-1-en-1-yl]oxy}(tert-butyl)dimethylsilane

HRID 271374
ノート
印刷プレビュー

反応式

HRID 271374 の反応式
C(Cl)Cl.[C:4]([O:12][CH:13]1[CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]1)(=O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(N(CC)C(C)C)(C)C.FC(F)(F)S(O[Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])(=O)=O>C(OCC)(=O)C.CCCCCC.O>[CH2:4]([O:12][CH:13]1[CH2:18][CH2:17][C:16]([O:19][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])=[CH:15][CH2:14]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 6344Dichloromethane2 回HCID 81531DiisopropylethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 2426774-(Benzoyloxy)cyclohexanone

生成物 1

HCID 68669646{[4-(Benzyloxy)cyclohex-1-en-1-yl]oxy}(tert-butyl)dimethylsilane収率 86.2%

試薬・触媒・溶媒 3

HCID 962
Water
溶媒
HCID 8058Hexane溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

A methylene chloride (200 mL) solution of 4-oxocyclohexyl benzoate [Macromolecules 2000, 33, 4619] (17.2 g, 84.5 mmol) in N,N-diisopropylethylamine (29.4 mL, 169 mmol) was cooled in an ice bath under nitrogen. A methylene chloride (50 mL) solution of tert-butyldimethylsilyl trifluormethanesulfonate (20.3 mL, 88.7 mmol) was added dropwise over 0.5 h. After warming to room temperature the contents of the reaction flask were poured into water. The organic layer was separated, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Flash column chromatography (hexane:ethyl acetate, 95:5) gave a pale oil (23.2 g, 86% yield).

後処理

  1. customThe organic layer was separated
  2. dry with materialdried with anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-11ceb7693dac4012ab5b02ec9bc40270
出典データセット
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07452893B2

反応ノート

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