2-Bromobenzyl alcohol → HCID 11989420, compound

HRID 2423269Notes

Reaction equation

HRID 2423269 reaction equation
C([Li])C[CH2:3][CH3:4].Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][OH:14].Cl[SiH2:16][CH:17]=C(C)C.[CH3:21]CCCCC.C(OCC)(=O)C>CCCCCC.C1COCC1.C(OCC)C>[OH:14][CH2:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[Si:16]([CH3:17])([CH3:21])[CH:3]=[CH2:4]

Participants

8

Reactant 4

HCID 728502-Bromobenzyl alcoholHCID 21226206Ethyl acetate hexaneHCID 57370515C4H9ClSiHCID 178418339Butyllithium

Product 1

HCID 11989420HCID 11989420, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

At −78° C., a 1.6 M solution of butyllithium (30 mL, 48 mmol) in hexane was added to a solution of 2-bromophenylmethanol (3.7 g, 20 mmol) in THF, and the resulting mixture was stirred at −78° C. for 1.5 hours. At −78° C., chloro(dimethyl)vinylsilane (7.2 g, 60 mmol) was added to the reacted mixture, and the resulting mixture was stirred for two hours. The resulting mixture solution was diluted with diethyl ether, and was washed with water and brine, and then was dried over anhydrous MgSO4. After removal of the solvents under reduced pressure, the residue was purified by flash chromatography on silica gel, thereby obtaining [2-(hydroxymethyl)phenyl]dimethyl(vinyl)silane: 1h (3.1 g, yield of 80%) as a colorless oil, Rf: 0.30 (hexane-ethyl acetate=7:1). 1H NMR (400 MHz, CDCl3) δ 7.56 (dd, J=7.3, 1.3 Hz, 1H), 7.46 (dd, J=7.1, 0.7 Hz, 1H), 7.41 (td, J=7.4, 1.5 Hz, 1H), 7.30 (td, J=7.3, 1.5 Hz, 1H), 6.39 (dd, J=20.3, 14.6 Hz, 1H), 6.08 (dd, J=14.6, 3.7 Hz, 1H), 5.79 (dd, J=20.3, 3.7 Hz, 1H), 4.74 (s, 2H), 1.71 (br s, 1H), 0.43 (s, 6H); 13C NMR (101 MHz, CDCl3) δ 146.4, 139.0, 136.2, 135.2, 132.8, 129.8, 128.0, 127.0, 65.3, −1.6; Anal. Calcd for C11H16Osi; C, 68.69; H, 8.39. Found: C, 68.43; H, 8.36.

Workup

  1. stirringthe resulting mixture was stirred for two hours
  2. washwas washed with water and brine
  3. dry with materialwas dried over anhydrous MgSO4
  4. customAfter removal of the solvents under reduced pressure
  5. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-533618b480f84a2ba63c637343d9bb44
Source dataset
uspto-grants-2011_06
Patent number
US07960571B2

Reaction notes

Loading…