Triethylamine → 2-[3-(Benzofuran-4-yl)phenyl]-4,4-dimethyl-4,5-dihydrooxazole

HRID 1740287Notes

Reaction equation

HRID 1740287 reaction equation
FC(F)(F)S(O[C:7]1[C:12]2[CH:13]=[CH:14][O:15][C:11]=2[CH:10]=[CH:9][CH:8]=1)(=O)=O.[CH3:18][C:19]1([CH3:33])[CH2:23][O:22][C:21]([C:24]2[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=2)=[N:20]1.C(N(CC)CC)C>CN(C)C=O>[O:15]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([C:26]3[CH:25]=[C:24]([C:21]4[O:22][CH2:23][C:19]([CH3:33])([CH3:18])[N:20]=4)[CH:29]=[CH:28][CH:27]=3)[C:12]=2[CH:13]=[CH:14]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 218381293-(4,4-Dimethyl-4,5-dihydrooxazol-2-yl)phenyldihydroxyboraneHCID 21838291Benzofuran-4-yl trifluoromethanesulfonate

Product 1

HCID 218382442-[3-(Benzofuran-4-yl)phenyl]-4,4-dimethyl-4,5-dihydrooxazoleYield 69.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4-trifluoromethylsulfonyloxy-benzofuran (2 g), 3-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)phenyldihydroxyborane (2.14 g), tetrakis(triphenyl-phosphine)palladium(0) (0.26 g) and triethylamine (2.28 g) in N,N-dimethylformamide (40 ml) was heated at 85° C. for 3 hours under nitrogen atmosphere. After evaporating the solvent, the residue was dissolved in a mixture of ethyl acetate (100 ml) and water (100 ml). The organic layer was successively washed with 10% sodium carbonate aqueous solution, brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica gel eluting with toluene. The fractions containing the desired products were collected and evaporated in vacuo to afford 2-[3-(benzofuran-4-yl)phenyl]-4,4-dimethyl-4,5-dihydrooxazole (1.52 g).

Workup

  1. customAfter evaporating the solvent
  2. dissolutionthe residue was dissolved in a mixture of ethyl acetate (100 ml) and water (100 ml)
  3. washThe organic layer was successively washed with 10% sodium carbonate aqueous solution, brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by column chromatography on silica gel eluting with toluene
  7. additionThe fractions containing the desired products
  8. customwere collected
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-1800dacb4d7b48099001b521ef37f276
Source dataset
uspto-grants-1999_10
Patent number
US05968985

Reaction notes

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