Benzyl Alcohol → HCID 12425357, compound

HRID 1700358Notes

Reaction equation

HRID 1700358 reaction equation
[O:1]=[C:2]([CH2:8][CH3:9])[CH2:3][C:4]([O:6][CH3:7])=[O:5].C(O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(OCC)(=O)C>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[O:1]=[C:2]([CH2:8][CH3:9])[CH2:3][C:4]([O:6][CH2:7][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:5]

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 8857Ethyl AcetateHCID 121699Methyl 3-oxovalerate

Product 1

HCID 12425357HCID 12425357, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

2.50 g (19.2 mmol) of methyl 3-oxovalerate, 6.23 g (57.6 mmol) of benzyl alcohol and 234 mg (1.92 mmol) of 4-dimethylaminopyridine were heated under reflux in 30 ml of toluene overnight. Ethyl acetate was added to the reaction solution. After washing with 1 N hydrochloric acid, the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1) to obtain the title compound.

Workup

  1. washAfter washing with 1 N hydrochloric acid
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-aa6d6847ce1f4950a61be32ce9464bf4
Source dataset
uspto-grants-2002_02
Patent number
US06350762B1

Reaction notes

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