Water → HCID 23090036, compound

HRID 1726326Notes

Reaction equation

HRID 1726326 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.C([Li])CCC.[O:15]1[CH2:20][CH2:19][C:18](=[O:21])[CH2:17][CH2:16]1.O>C1COCC1>[OH:21][C:18]1([C:2]2[CH:3]=[C:4]([CH3:9])[CH:5]=[C:6]([CH3:8])[CH:7]=2)[CH2:19][CH2:20][O:15][CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 121599Tetrahydro-4H-pyran-4-oneHCID 136357Benzene, 1-bromo-3,5-dimethyl-HCID 178418339Butyllithium

Product 1

HCID 23090036HCID 23090036, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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

Workup

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

Sources & evidence

ORD record
ord-b6264551f3034a86bb216f4cd94bc27a
Source dataset
uspto-grants-2009_02
Patent number
US07491748B2

Reaction notes

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