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

HRID 2180591ノート

反応式

HRID 2180591 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-761e86263d3f4109af3dca61d6e4105c
出典データセット
uspto-grants-2005_05
特許番号
US06887896B1

反応ノート

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