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

HRID 471293

反応式

HRID 471293 の反応式
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]

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒HCID 522689Potassium Fluoride溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-902f7da4fb3e47b1af6d857ad950fbb6
出典データセット
uspto-grants-2014_01
特許番号
US08629271B2

関連ノート

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