Tributylvinyltin → HCID 86675861, compound

HRID 1895776Notes

Reaction equation

HRID 1895776 reaction equation
Br[C:2]1[CH:3]=[C:4]([C@H:8]([OH:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[CH2:11]([Sn](CCCC)(CCCC)C=C)[CH2:12]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>[CH:11]([C:2]1[CH:3]=[C:4]([C@H:8]([OH:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1)=[CH2:12]

Participants

5

Reactant 2

HCID 81998Tributylvinyltin2×HCID 2734889(R)-1-(3-Bromophenyl)ethanol

Product 1

HCID 86675861HCID 86675861, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalyst2×HCID 1140TolueneSolvent

Conditions

Temperature
45 °C

Procedure

Bis(triphenylphosphine)palladium(II) dichloride (360 mg, 0.512 mmol) was added to a degassed solution of (R)-1-(3-bromo-phenyl)-ethanol (1.03 g, 5.123 mmol) and tributyl(vinyl)tin (1.8 ml, 6.15 mmol) in toluene (10 ml) under N2 and the reaction was stirred at 45° C. for 18 h. Tributyl(vinyl)tin (2.56 mmol, 750 uL) and bis(triphenylphosphine)palladium(II) dichloride (0.256 mmol, 180 mg) were added and stirring was continued for 18 h. The reaction was cooled and the solvent evaporated to afford a residue which was absorbed onto SiO2. Purification by SiO2 (3:1 i-hexane/ethyl acetate) afforded 13a as a yellow oil (675 mg, 89%). 1H NMR (300 MHz, CDCl3) δ7.49 (1H, s), 7.33 (3H, m), 6.75 (1H, dd, J=17.6, 10.9 Hz), 5.80 (1H, d, J=17.6 Hz), 5.28 (1H, d, J=10.7 Hz), 4.93 (1H, m), 1.81 (1H, d, J=3.1 Hz), 1.52 (3H, d, J=6.5 Hz).

Workup

  1. stirringstirring
  2. waitwas continued for 18 h
  3. temperatureThe reaction was cooled
  4. customthe solvent evaporated
  5. customto afford a residue which
  6. customwas absorbed onto SiO2
  7. customPurification by SiO2 (3:1 i-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-0a9d629621e64d0aa30c06d5b5436da2
Source dataset
uspto-grants-2013_08
Patent number
US08513184B2

Reaction notes

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