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

HRID 1790209Notes

Reaction equation

HRID 1790209 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

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 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 (Mg2SO4), 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, 6 H), 1.32 (s, 6 H), 1.79 (m, 1 H), 2.40 (d, J=6.9 Hz, 2 H), 4.20 (s, 2 H), 6.68 (dd, J=1.2 Hz and 7.5 Hz, 1 H), 6.87 (m, 2 H).

Workup

  1. customthe layers separated
  2. washThe organic layer was further washed with water, aqueous NaHCO3 and brine
  3. dry with materialdried (Mg2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified on silica gel (0% to 5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-901ce828923d41e8b5486673c213dff6
Source dataset
uspto-grants-2006_07
Patent number
US07071218B2

Reaction notes

Loading…