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

HRID 460281노트

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HRID 460281 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 220413975-Isobutyl-3,3-dimethyl-2,3-dihydro-benzofuran수율 87.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-4ed9ed13b1aa4f3ca71253771bd021cc
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196108B2

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