Stannane, tributyl(1-ethoxyethenyl)- → 3-(1-((tert-butyldimethylsilyl)oxy)ethyl)-4-vinyl-1H-isochromen-1-one

HRID 634378Notes

Reaction equation

HRID 634378 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[O:4][C:3]=1[CH:13]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH3:14].[CH2:23]([Sn](CCCC)(CCCC)C(OCC)=C)[CH2:24]CC>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Si:16]([O:15][CH:13]([C:3]1[O:4][C:5](=[O:12])[C:6]2[C:11]([C:2]=1[CH:23]=[CH2:24])=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH3:14])([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

5

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 1239597364-bromo-3-(1-((tert-butyldimethylsilyl)oxy)ethyl)-1H-isochromen-1-one2×

Product 1

HCID 1232000243-(1-((tert-butyldimethylsilyl)oxy)ethyl)-4-vinyl-1H-isochromen-1-one

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalyst2×HCID 1140TolueneSolvent

Procedure

To a degassed solution of 4-bromo-3-(1-((tert-butyldimethylsilyl)oxy)ethyl)-1H-isochromen-1-one (intermediate A8, 6 g, 15.7 mmol) in toluene (120 ml), PdCl2(PPh3)2 (0.6 g, 079 mmol) was added followed by tributyl(1-ethoxyvinyl)tin (5 ml, 17.2 mmol) and the resulting mixture was heated to reflux overnight. Additional PdCl2(PPh3)2 (0.6 g) was added at room temperature, and the mixture was refluxed for 30 minutes. The mixture was cooled to room temperature, then filtered through a celite pad. The filtrate was evaporated to dryness and the crude was purified by flash chromatography on Biotage silica gel cartridges (cyclohexane to cyclohexane:EtOAc=80:20) to afford 3-(1-((tert-butyldimethylsilyl)oxy)ethyl)-4-vinyl-1H-isochromen-1-one as a pale yellow oil (Intermediate B59.1, 5.8 g).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux overnight
  3. temperaturethe mixture was refluxed for 30 minutes
  4. filtrationfiltered through a celite pad
  5. customThe filtrate was evaporated to dryness
  6. customthe crude was purified by flash chromatography on Biotage silica gel cartridges (cyclohexane to cyclohexane:EtOAc=80:20)

Sources & evidence

ORD record
ord-a94899a4e5a04923bdb72aa811f617a5
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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