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

HRID 271374
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HRID 271374 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 6344Dichloromethane2회HCID 81531DiisopropylethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 2426774-(Benzoyloxy)cyclohexanone

생성물 1

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

시약·촉매·용매 3

HCID 962
Water
용매
HCID 8058Hexane용매
HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-11ceb7693dac4012ab5b02ec9bc40270
출처 데이터셋
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07452893B2

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