Triethylamine → Benzofuran-5-yl(phenyl)methanone

HRID 2075192

Reaction equation

HRID 2075192 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[OH:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1.C(N(CC)CC)C.C(Cl)Cl.CS(C)=O>CS(C)=O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[O:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21912085Dimethylsulfoxide-dichloromethaneHCID 58415371Benzofuran-5-yl(phenyl)methanol

Product 1

HCID 58415352Benzofuran-5-yl(phenyl)methanone

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of benzofuran-5-yl(phenyl)methanol (4.0 g, 18 mmol) and triethylamine (7.3 mL, 54 mmol) in 30 mL 1:1 DCM/DMSO under nitrogen at 0° C. was added a solution of SO3*py (8.5 g, 54 mmol) in 20 mL DMSO dropwise via addition funnel. The reaction was allowed to stir 5 h at 0° C. and was quenched by addition of water and 250 mL Et2O. The organic layer was washed with water, 1N HCl, 1N NaOH, brine, and was dried over sodium sulfate, filtered, and concentrated. The resulting solid benzofuran-5-yl(phenyl)methanone was used without further purification. MS (ESI) m/z: Calculated: 222.1; Observed: 223.0 (M++1).

Workup

  1. additiondropwise via addition funnel
  2. customwas quenched by addition of water and 250 mL Et2O
  3. washThe organic layer was washed with water, 1N HCl, 1N NaOH, brine
  4. dry with materialwas dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting solid benzofuran-5-yl(phenyl)methanone was used without further purification

Sources & evidence

ORD record
ord-770de3bda5be496e98d3f55f52d5696b
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Linked notes

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