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

HRID 716813노트

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HRID 716813 반응식
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

참가 물질

5

반응물 3

HCID 962WaterHCID 25134Boron tribromideHCID 867156956-methoxy-4,4-dimethyl-3,4-dihydro-1H-isochromene2회

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-08fb9b5bbbf14317a1cc6f6eabf354a4
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193704B2

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