Boron tribromide → 5,6,7,8,8a,9-hexahydro-4bH-fluoren-2-ol

HRID 237762ノート

反応式

HRID 237762 の反応式
C[O:2][C:3]1[CH:15]=[C:14]2[C:6]([CH:7]3[CH:12]([CH2:13]2)[CH2:11][CH2:10][CH2:9][CH2:8]3)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[CH:15]1[C:14]2[CH2:13][CH:12]3[CH:7]([CH2:8][CH2:9][CH2:10][CH2:11]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[OH:2]

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 685247797-methoxy-2,3,4,4a,9,9a-hexahydro-1H-fluorene

生成物 1

HCID 685276645,6,7,8,8a,9-hexahydro-4bH-fluoren-2-ol収率 81.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To 7-methoxy-2,3,4,4a,9,9a-hexahydro-1H-fluorene (1.95 g, 9.65 mmol) in CH2Cl2 (20 mL) was added BBr3 (1M in CH2Cl2, 24 mmol) dropwise at 0° C. This mixture was stirred at 0° C. for one hour. The reaction mixture was then quenched with MeOH (5 mL). Aqueous sodium hydrogen carbonate (10 mL) was added. The reaction mixture was stirred at room temperature overnight. The reaction mixture was extracted with CH2Cl2. The organic phase was washed with brine, dried (Na2SO4) and concentrated. Silica gel chromatography (EtOAc/heptane) provided 1.48 g of 5,6,7,8,8a,9-hexahydro-4bH-fluoren-2-ol.

後処理

  1. customThe reaction mixture was then quenched with MeOH (5 mL)
  2. additionAqueous sodium hydrogen carbonate (10 mL) was added
  3. stirringThe reaction mixture was stirred at room temperature overnight
  4. extractionThe reaction mixture was extracted with CH2Cl2
  5. washThe organic phase was washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-4f2b34b4d6364c17a2c519c7d3a8a763
出典データセット
uspto-grants-2014_02
特許番号
US08642603B2

反応ノート

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