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

HRID 1883265ノート

反応式

HRID 1883265 の反応式
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

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 30179161-(5,6,7,8-Tetrahydro-3-methoxy-5,5,8,8-tetramethyl-2-naphthyl)ethan-1-one2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-c26792f6ec9b4a26b3c5a26a47170c37
出典データセット
uspto-grants-2004_07
特許番号
US06759547B1

反応ノート

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