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

HRID 716812ノート

反応式

HRID 716812 の反応式
[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]

参加物

5

反応物 2

HCID 962WaterHCID 867156941-Methoxy-3-[2-(methoxymethoxy)-1,1-dimethyl-ethyl]benzene2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3ee339be03f0471abc4b5728a6abdd50
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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