Phenol → Phenoxymethyl ketone

HRID 225948

반응식

HRID 225948 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 13408090Phenoxymethyl ketone수율 50%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

출처 및 근거

ORD 기록
ord-8187fab915144f549df77aa45aa50258
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557133B2

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