Water → 5-Isobutyl-3,3-dimethyl-2,3-dihydro-benzofuran

HRID 460281ノート

反応式

HRID 460281 の反応式
[CH3:1][C:2]1([CH3:16])[C:6]2[CH:7]=[C:8]([CH:11](O)[CH:12]([CH3:14])[CH3:13])[CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.O>ClCCl>[CH2:11]([C:8]1[CH:9]=[CH:10][C:5]2[O:4][CH2:3][C:2]([CH3:1])([CH3:16])[C:6]=2[CH:7]=1)[CH:12]([CH3:14])[CH3:13]

参加物

6

反応物 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 220414081-(3,3-Dimethyl-2,3-dihydrobenzofuran-5-yl)-2-methyl-propan-1-ol

生成物 1

HCID 220413975-Isobutyl-3,3-dimethyl-2,3-dihydro-benzofuran収率 87.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a cold solution (0° C.) of 1-(3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-2-methyl-propan-1-ol (1.97 g, 8.93 mmol) in dry dichloromethane (40 mL) was added triethylsilane (2.85 mL, 17.86 mmol). After 10 minutes, trifluoroacetic acid was added and the reaction mixture stirred at 0° C. for 30 minutes. Water was poured into the reaction mixture and the layers separated. The organic layer was further washed with water, aqueous NaHCO3 and brine, dried (MgSO4), filtered and evaporated. The residue was purified on silica gel (0% to 5% ethyl acetate in hexane) to give 1.6 g of 5-isobutyl-3,3-dimethyl-2,3-dihydro-benzofuran (87%). 1H NMR (300 MHz; CDCl3): δ 0.90 (d, J=6.3 Hz, 6H), 1.32 (s, 6H), 1.79 (m, 1H), 2.40 (d, J=6.9 Hz, 2H), 4.20 (s, 2H), 6.68 (dd, J=1.2 Hz and 7.5 Hz, 1H), 6.87 (m, 2H).

後処理

  1. customthe layers separated
  2. washThe organic layer was further washed with water, aqueous NaHCO3 and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified on silica gel (0% to 5% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-4ed9ed13b1aa4f3ca71253771bd021cc
出典データセット
uspto-grants-2007_03
特許番号
US07196108B2

反応ノート

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