Boron tribromide → 5,6,7,8-Tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2-naphthyl methyl ketone

HRID 1883265노트

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HRID 1883265 반응식
C[O:2][C:3]1[C:4]([C:17](=[O:19])[CH3:18])=[CH:5][C:6]2[C:7]([CH3:16])([CH3:15])[CH2:8][CH2:9][C:10]([CH3:14])([CH3:13])[C:11]=2[CH:12]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[C:4]([C:17](=[O:19])[CH3:18])=[CH:5][C:6]2[C:7]([CH3:16])([CH3:15])[CH2:8][CH2:9][C:10]([CH3:13])([CH3:14])[C:11]=2[CH:12]=1

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 30179161-(5,6,7,8-Tetrahydro-3-methoxy-5,5,8,8-tetramethyl-2-naphthyl)ethan-1-one2회

생성물 1

HCID 2266995,6,7,8-Tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2-naphthyl methyl ketone수율 75%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a solution of 1-(3-methoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone (Intermediate 3, 10.7 g, 41.2 mmol) in CH2Cl2 (500 mL) at 0° C. was added BBr3 (49.5 mL, 1.0 M in CH2Cl2) via syringe pump over 10 min. The mixture was stirred at 0° C. for 2 h and was quenched with ice-H2O and extracted with Et2O (×3). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (CH2Cl2) to give the title compound as a brown solid (7.6 g, 75%).

후처리

  1. customwas quenched with ice-H2O
  2. extractionextracted with Et2O (×3)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel (CH2Cl2)

출처 및 근거

ORD 기록
ord-c26792f6ec9b4a26b3c5a26a47170c37
출처 데이터셋
uspto-grants-2004_07
특허 번호
US06759547B1

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