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

HRID 471293
Notes
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Reaction equation

HRID 471293 reaction equation
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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 167845
palladium(II) acetate
Catalyst
HCID 1140TolueneSolvent
HCID 8857Ethyl AcetateSolvent
HCID 522689Potassium FluorideSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-902f7da4fb3e47b1af6d857ad950fbb6
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08629271B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes