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Triethylamine → 2-(Tert-butyldimethylsilanyloxy)-1-phenylethanone

HRID 77324
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반응식

HRID 77324 반응식
[OH:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].C(N(CC)CC)C.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>ClCCl.CN(C)C1C=CN=CC=1>[C:21]([Si:18]([CH3:20])([CH3:19])[O:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4])([CH3:24])([CH3:23])[CH3:22]
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참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 68490alpha-Hydroxyacetophenone

생성물 1

HCID 135233382-(Tert-butyldimethylsilanyloxy)-1-phenylethanone수율 70.7%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344
Dichloromethane
용매
3회

실험 절차

To a well stirred solution of 2-hydroxyacetophenone (1.0 g, 7.34 mmol) in dichloromethane (15 mL) is added triethylamine (1.23 mL, 8.81 mmol), 4-dimethylaminopyridine (45 mg, 0.367 mmol) and tert-butyldimethylsilyl chloride (1.16 g, 7.71 mmol) dissolved in dichloromethane (2 mL). The reaction mixture is stirred at room temperature for 1 h, then diluted with dichloromethane (50 mL), washed with 10% citric acid, saturate sodium carbonate, brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified via silica gel chromatography (20% ethyl acetate in hexanes) to yield the title compound as a yellow oil (1.3 g, 5.19 mmol).

후처리

  1. washwashed with 10% citric acid
  2. concentrationsaturate sodium carbonate, brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified via silica gel chromatography (20% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-bc682cb8ff3148aa8529b9d5ab9e350a
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08841291B2

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