Water → 4,4-dimethyl-3,4-dihydro-1H-isochromen-6-ol

HRID 716813ノート

反応式

HRID 716813 の反応式
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][O:8][CH2:7][C:6]2([CH3:14])[CH3:13].BrB(Br)Br.O>C(Cl)Cl>[CH3:13][C:6]1([CH3:14])[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([OH:2])[CH:4]=2)[CH2:9][O:8][CH2:7]1

参加物

5

反応物 3

HCID 962WaterHCID 25134Boron tribromideHCID 867156956-methoxy-4,4-dimethyl-3,4-dihydro-1H-isochromene2 回

生成物 1

HCID 714912434,4-dimethyl-3,4-dihydro-1H-isochromen-6-ol収率 12.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

6-methoxy-4,4-dimethyl-3,4-dihydro-1H-isochromene (Intermediate 41, 350 mg, 1.8205 mmol) was dissolved in DCM (10 mL) and the solution was cooled to 0° C. Tribromoborane (228.04 mg, 0.9102 mmol) was added and the resulting mixture was stirred at 0° C. for 2 hours. Water (10 mL) was added and the two phases were separated. Organics were dried over Na2SO4, filtered and dried in vacuo. The crude was purified by flash chromatography (Biotage system) on silica gel using a SNAP 25 g as column and cyclohexane/ethyl acetate from 100:0 to 70:30 as eluent affording the title compound (42 mg).

後処理

  1. customthe two phases were separated
  2. dry with materialOrganics were dried over Na2SO4
  3. filtrationfiltered
  4. customdried in vacuo
  5. customThe crude was purified by flash chromatography (Biotage system) on silica gel using a SNAP 25 g as column and cyclohexane/ethyl acetate from 100:0 to 70:30 as eluent

出典と根拠

ORDレコード
ord-08fb9b5bbbf14317a1cc6f6eabf354a4
出典データセット
uspto-grants-2015_11
特許番号
US09193704B2

反応ノート

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