Phenol → Phenoxymethyl ketone

HRID 225948

Reaction equation

HRID 225948 reaction equation
Br[CH2:2][C:3]([CH2:5]Br)=[O:4].[C:7]1([OH:13])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[F-].[K+]>CN(C)C=O>[O:4]([CH2:8][C:7]([CH2:12][O:13][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:13])[C:3]1[CH:5]=[CH:11][CH:10]=[CH:9][CH:2]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 699521,3-Dibromo-2-propanoneHCID 522689Potassium Fluoride

Product 1

HCID 13408090Phenoxymethyl ketoneYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Thus obtained bromomethyl ketone derivative (X, 12.9 g, 31.0 mmol) and phenol (3.23 g, 1.2 Eq) were dissolved in dimethylformamide (30 ml), KF(4.53 g, 2.5 Eq) was added, and the mixture was stirred for two hours to give phenoxymethyl ketone derivative (XIb). This compound was dissolved in methanol (40 ml)-THF (100 ml) and was reacted by adding NaBH4 (2.35 g)-methanol solution (40 ml) (−10□-room temperature, two hours). The reaction was stopped by acetic acid, and the reaction mixture was distilled under reduced pressure to remove methanol. The residue was extracted with ethyl acetate (50 ml×2), washed with water and aqueous sodium chloride solution, dried (anhydrous Na2SO4), concentrated under reduced pressure, and separated-purified by column chromatography (ethyl acetate-hexane, 1:7) to give a compound (XIIb, 6.50 g, Yield 50%) in a diastereomeric form of which amino group is protected by benzyloxycarbonyl.

Sources & evidence

ORD record
ord-8187fab915144f549df77aa45aa50258
Source dataset
uspto-grants-2009_07
Patent number
US07557133B2

Linked notes

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