p-Toluenesulfonic acid monohydrate → 5-Bromo-7-[2-(2,2-dimethyl-4-trifluoromethyl-[1,3]dioxolan-4-yl)-1,1-dimethylethyl]-2,3-dihydrobenzofuran

HRID 2106038ノート

反応式

HRID 2106038 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([C:11]([CH3:22])([CH3:21])[CH2:12][C:13]([C:17]([F:20])([F:19])[F:18])([OH:16])[CH2:14][OH:15])[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.O.[C:24]1(C)[CH:29]=CC(S(O)(=O)=O)=C[CH:25]=1>CC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:11]([CH3:22])([CH3:21])[CH2:12][C:13]2([C:17]([F:20])([F:18])[F:19])[CH2:14][O:15][C:24]([CH3:29])([CH3:25])[O:16]2)[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1

参加物

4

反応物 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 578098304-(5-Bromo-2,3-dihydrobenzofuran-7-yl)-4-methyl-2-trifluoromethylpentane-1,2-diol

生成物 1

HCID 578099225-Bromo-7-[2-(2,2-dimethyl-4-trifluoromethyl-[1,3]dioxolan-4-yl)-1,1-dimethylethyl]-2,3-dihydrobenzofuran収率 372.1%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A mixture of 7.6 g (20 mmol) of 4-(5-bromo-2,3-dihydrobenzofuran-7-yl)-4-methyl-2-trifluoromethylpentane-1,2-diol and 0.754 g (4 mmol) of p-toluenesulfonic acid monohydrate in 200 mL of acetone was stirred at room temperature for 6 days and the volatiles removed in vacuo. The residue was dissolved in EtOAc, washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, and concentrated in vacuo. The residue was extracted with diethyl ether and the filtrate concentrated in vacuo to afford 6.3 g (75%) of 5-bromo-7-[2-(2,2-dimethyl-4-trifluoromethyl-[1,3]dioxolan-4-yl)-1,1-dimethylethyl]-2,3-dihydrobenzofuran.

後処理

  1. customthe volatiles removed in vacuo
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with saturated aqueous sodium bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. extractionThe residue was extracted with diethyl ether
  7. concentrationthe filtrate concentrated in vacuo

出典と根拠

ORDレコード
ord-72d674eedc8046e090b45209707e79fd
出典データセット
uspto-grants-2009_08
特許番号
US07579469B2

反応ノート

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