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Isopropenyl acetate → 1-(3-((tert-Butyldimethylsilyloxy)methyl)phenyl)propan-2-one

HRID 471293
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인쇄 미리보기

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HRID 471293 반응식
Br[C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].C([O:20][C:21]([CH3:23])=[CH2:22])(=O)C.C[O-].C([Sn+](CCCC)CCCC)CCC.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C1(C)C=CC=CC=1.C(OCC)(=O)C.[F-].[K+].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Si:7]([O:6][CH2:5][C:4]1[CH:3]=[C:2]([CH2:22][C:21](=[O:20])[CH3:23])[CH:16]=[CH:15][CH:14]=1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]
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참가 물질

9

반응물 4

HCID 7916Isopropenyl acetateHCID 80271Tri-o-tolylphosphineHCID 11964040Methoxytri-n-butylstannaneHCID 220331471-Bromo-3-((((1,1-dimethylethyl)dimethylsilyl)oxy)methyl)benzene

생성물 1

HCID 579892691-(3-((tert-Butyldimethylsilyloxy)methyl)phenyl)propan-2-one

시약·촉매·용매 4

HCID 167845
palladium(II) acetate
촉매
HCID 1140Toluene용매
HCID 8857Ethyl Acetate용매
HCID 522689Potassium Fluoride용매

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온도
100 °C

실험 절차

A mixture of (3-bromobenzyloxy)(tert-butyl)dimethylsilane (16.72 g), isopropenyl acetate (9.2 mL), tri-n-butyltin methoxide (24 mL), palladium(II)acetate (0.625 g) and tri(o-tolyl)phosphine (1.70 g) in anhydrous toluene (65 mL) was heated at reflux at 100° C. for 5 hours and then left to cool overnight. The mixture was diluted with ethyl acetate (130 mL) and 4 molar aqueous potassium fluoride (80 mL) and stirred vigorously for 20 minutes. Diatomaceous earth was added and the suspension was then filtered through diatomaceous earth, washing the residue well with ethyl acetate. The combined filtrate and washings were dried over anhydrous magnesium sulphate and concentrated in vacuo and purified by flash chromatography on silica eluting with isohexane, 10% dichloromethane in isohexane and 20% diethyl ether in isohexane to afford the subtitled compound as a yellow oil. Yield 13.71 g.

후처리

  1. temperaturewas heated
  2. waitleft
  3. temperatureto cool overnight
  4. additionDiatomaceous earth was added
  5. filtrationthe suspension was then filtered through diatomaceous earth
  6. washwashing the residue well with ethyl acetate
  7. dry with materialThe combined filtrate and washings were dried over anhydrous magnesium sulphate
  8. concentrationconcentrated in vacuo
  9. custompurified by flash chromatography on silica eluting with isohexane, 10% dichloromethane in isohexane and 20% diethyl ether in isohexane

출처 및 근거

ORD 기록
ord-902f7da4fb3e47b1af6d857ad950fbb6
출처 데이터셋
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08629271B2

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