Dimethylformamide → 1-(5-Methoxy-3-methyl-1-benzofuran-2-yl)-2,2-dimethylpropan-1-one

HRID 2103752Notes

Reaction equation

HRID 2103752 reaction equation
CN(C=O)C.[OH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=1[C:15](=O)[CH3:16].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:25][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28]>O>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]2[O:6][C:25]([C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])=[C:15]([CH3:16])[C:8]=2[CH:9]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 21642BromopinacoloneHCID 697141-(2-Hydroxy-5-methoxyphenyl)ethan-1-one

Product 1

HCID 288262421-(5-Methoxy-3-methyl-1-benzofuran-2-yl)-2,2-dimethylpropan-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

DMF (4 mL) was added to a mixture of 166 mg 1-(2-hydroxy-5-methoxyphenyl)ethanone and 370 mg cesium carbonate followed by 188 mg 1-bromopinacolone. After heating this mixture in an 85° C. oil bath for 3 hours, it was poured into cold water and extracted with ether. The combined ether extract was washed with water, 1.5 N NaOH, water, and saturated brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to give a crude product. It was purified on silica gel (9:1 hexanes and EtOAc) to give the title compound as a colorless solid. 1H NMR (CDCl3, 500 MHz) δ 7.41 (d, J=9.0 Hz, 1H), 7.11 (dd, J=2.5 & 9.0 Hz, 1H), 7.04 (d, J=2.5 Hz, 1H), 3.90 (s, 3H), 2.59 (s, 3H), 1.43 (s, 9H).

Workup

  1. extractionextracted with ether
  2. extractionThe combined ether extract
  3. washwas washed with water, 1.5 N NaOH, water, and saturated brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto give a crude product
  7. customIt was purified on silica gel (9:1 hexanes and EtOAc)

Sources & evidence

ORD record
ord-3e2609893e1a4df6816fe81481d95da9
Source dataset
uspto-grants-2009_08
Patent number
US07576122B2

Reaction notes

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