N-bromobutanimide → 1-(4-Bromo-3-hydroxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone

HRID 2180591노트

반응식

HRID 2180591 반응식
[OH:1][C:2]1[C:3]([C:14](=[O:16])[CH3:15])=[CH:4][C:5]2[CH2:6][CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.[Br:17]N1C(=O)CCC1=O>CN(C)C=O.O>[Br:17][C:11]1[C:10]2[C:9]([CH3:12])([CH3:13])[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[C:3]([C:14](=[O:16])[CH3:15])[C:2]=1[OH:1]

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 224907981-(3-Hydroxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone

생성물 1

HCID 224908841-(4-Bromo-3-hydroxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 1-(3-hydroxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone (Compound A-88, 13.3 g, 61 mmol) in N,N-dimethylformamide (120 mL) was added N-bromosuccinimide (10.9 mg, 61 mmol). The mixture was stirred at room temperature for 16 h. The mixture was then diluted with water and extracted with diethyl ether. The combined ethereal layers were washed with water, brine, dried (Na2SO4), filtered and concentrated in vacuo. Recrystallization from diethyl ether and flash column chromatography (silica gel, 5% ethyl acetate in hexane) afforded the title compound as a yellow solid.

후처리

  1. extractionextracted with diethyl ether
  2. washThe combined ethereal layers were washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customRecrystallization from diethyl ether and flash column chromatography (silica gel, 5% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-761e86263d3f4109af3dca61d6e4105c
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06887896B1

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