Triethylsilane → 3-(4-Bromo-3,5-dimethylphenyl)-2,5-dihydrofuran

HRID 237582Notes

Reaction equation

HRID 237582 reaction equation
C([SiH](CC)CC)C.[Br:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]2[CH:20]=[CH:19][O:18][CH:17]=2)=[CH:11][C:10]=1[CH3:21].C([O-])(O)=O.[Na+]>FC(F)(F)C(O)=O>[Br:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]2[CH2:17][O:18][CH2:19][CH:20]=2)=[CH:11][C:10]=1[CH3:21]

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 866972453-(4-Bromo-3,5-dimethylphenyl)furan

Product 1

HCID 866972463-(4-Bromo-3,5-dimethylphenyl)-2,5-dihydrofuran

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Triethylsilane (3.67 mL) is added dropwise to a solution of 3-(4-bromo-3,5-dimethylphenyl)furan (580 mg) in trifluoroacetic acid and the resulting mixture is stirred at room temperature for 3 h. Saturated aqueous NaHCO3 solution is added and the aqueous phase is separated and extracted with ethyl acetate. The combined extracts are washed with brine, dried over MgSO4 and concentrated in vacuo. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 95:5) to give the title compound. LC (method 9): tR=1.16 min; Mass spectrum (ESI+): m/z=251, 253 [M+H]+.

Workup

  1. customthe aqueous phase is separated
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts are washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 95:5)

Sources & evidence

ORD record
ord-1bfc0fa76d704a7da2e2c263c18761b5
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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