Water → HCID 65624342, compound

HRID 1663593Notes

Reaction equation

HRID 1663593 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.O.[C:11](=[O:13])=O.[CH3:14][C:15]([CH3:17])=O>O1CCCC1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([C:15]2[CH:17]=[CH:6][C:5]([CH2:8][O:13][CH3:11])=[CH:4][CH:14]=2)[OH:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 77264-ChlorobenzaldehydeHCID 18522661Acetone cardice

Product 1

HCID 65624342HCID 65624342, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound obtained in the above step (2) (515 mg) in tetrahydrofaran (4 mL) was added dropwise 1.59M butyl lithium-hexane solution (1.61 mL) under nitrogen gas atmosphere and cooling in dry ice/acetone bath and the mixture was stirred for 10 minutes. Thereto was added a solution of 4-chlorobenzaldehyde (360 mg) in tetrahydrofuran (1 mL) and the mixture was stirred at room temperature overnight. To the reaction mixture was added water and the mixture was extracted with ethyl acetate (×2). The organic layer was concentrated in vacuo and the resultant crude product was purified by a column chromatography on silica gel (solvent; hexane/ethyl acetate=80:20→60:40) to give (4-chlorophenyl)[4-(methoxymethyl)phenyl]methanol (459 mg, yield: 68%) as an oil.

Workup

  1. customTo a solution of the compound obtained in the above step (2) (515 mg) in tetrahydrofaran (4 mL)
  2. additionwas added dropwise 1.59M butyl lithium-hexane solution (1.61 mL) under nitrogen gas atmosphere
  3. stirringthe mixture was stirred at room temperature overnight
  4. extractionthe mixture was extracted with ethyl acetate (×2)
  5. concentrationThe organic layer was concentrated in vacuo
  6. customthe resultant crude product was purified by a column chromatography on silica gel (solvent; hexane/ethyl acetate=80:20→60:40)

Sources & evidence

ORD record
ord-dca9165dc12e4f788554b79d5f8c3c1f
Source dataset
uspto-grants-2011_10
Patent number
US08034949B2

Reaction notes

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