Water → HCID 23090036, compound

HRID 2103748Notes

Reaction equation

HRID 2103748 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[O:10]1[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]1.O>C1COCC1.C([Li])CCC.C(OCC)(=O)C>[OH:16][C:13]1([C:2]2[CH:3]=[C:4]([CH3:9])[CH:5]=[C:6]([CH3:8])[CH:7]=2)[CH2:14][CH2:15][O:10][CH2:11][CH2:12]1

Participants

7

Reactant 3

HCID 962WaterHCID 121599Tetrahydro-4H-pyran-4-oneHCID 136357Benzene, 1-bromo-3,5-dimethyl-

Product 1

HCID 23090036HCID 23090036, compoundYield 63.1%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 178418339ButyllithiumSolvent

Procedure

Under an atmosphere of argon, to a solution of 5-bromo-m-xylene (5.55 g) in THF (60 mL), n-butyl lithium (17.8 mL) was added at −78° C. The mixture was stirred for 1 hour. Tetrahydropyran-4-on (2.0 g) was added to the reaction mixture, and the mixture was stirred for 3 hours. Water was added to the reaction mixture, and the solution was diluted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:3) to give the title compound (2.6 g) having the following physical data.

Workup

  1. stirringthe mixture was stirred for 3 hours
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride, dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:3)

Sources & evidence

ORD record
ord-c1ed8d321aa74f1f922ad11f48a88a91
Source dataset
uspto-grants-2009_08
Patent number
US07576129B2

Reaction notes

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