Water → 6-methoxy-4,4-dimethyl-3,4-dihydro-1H-isochromene

HRID 716812노트

반응식

HRID 716812 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([CH3:16])([CH3:15])[CH2:10][O:11][CH2:12]OC)[CH:4]=1.O>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6](=[CH:7][CH:8]=1)[CH2:12][O:11][CH2:10][C:9]2([CH3:16])[CH3:15]

참가 물질

5

반응물 2

HCID 962WaterHCID 867156941-Methoxy-3-[2-(methoxymethoxy)-1,1-dimethyl-ethyl]benzene2회

생성물 1

HCID 867156956-methoxy-4,4-dimethyl-3,4-dihydro-1H-isochromene수율 136.1%

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 6344Dichloromethane용매

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온도
-78 °C

실험 절차

1-methoxy-3-[2-(methoxymethoxy)-1,1-dimethyl-ethyl]benzene (Intermediate 40, 300 mg, 1.3375 mmol) was dissolved in DCM (8 mL), the solution was cooled to −78° C. and titanium tetrachloride (37.928 mg, 0.2000 mmol) was added dropwise. The resulting mixture was stirred at room temperature for 2 hours. water (15 mL) was added and the mixture extracted with EtOAc (25 mL). Organics were dried over Na2SO4, filtered and evaporated to afford a crude that 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 90:10 as eluent affording the title compound (350 mg).

후처리

  1. extractionthe mixture extracted with EtOAc (25 mL)
  2. dry with materialOrganics were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customto afford a crude that
  6. customwas purified by flash chromatography (Biotage system) on silica gel using a SNAP 25 g as column and cyclohexane/ethyl acetate from 100:0 to 90:10 as eluent

출처 및 근거

ORD 기록
ord-3ee339be03f0471abc4b5728a6abdd50
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193704B2

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