N-methoxy-N-methyl-5-phenylfuran-2-carboxamide → (5-Phenylfuran-2-yl)(3,4,5-trimethoxyphenyl)methanone

HRID 63189Notes

Reaction equation

HRID 63189 reaction equation
CON(C)[C:4]([C:6]1[O:7][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:9][CH:10]=1)=[O:5].[CH3:18][O:19][C:20]1[CH:21]=[C:22]([Mg]Br)[CH:23]=[C:24]([O:28][CH3:29])[C:25]=1[O:26][CH3:27]>C1COCC1>[C:11]1([C:8]2[O:7][C:6]([C:4]([C:22]3[CH:23]=[C:24]([O:28][CH3:29])[C:25]([O:26][CH3:27])=[C:20]([O:19][CH3:18])[CH:21]=3)=[O:5])=[CH:10][CH:9]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 17832042N-methoxy-N-methyl-5-phenylfuran-2-carboxamideHCID 178492974HCID 178492974, compound

Product 1

HCID 53364050(5-Phenylfuran-2-yl)(3,4,5-trimethoxyphenyl)methanoneYield 35.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 38d (0.231 g, 1 mmoL) in 5 mL THF was added a THF solution of 3,4,5-trimethoxyphenylmagnesiumbromide (0.5 N, 4.0 mL, 2 mmol) at 0° C. The mixture was allowed to stir for 30 min and quenched with water, extracted with ethyl acetate and dried with MgSO4. The solvent was removed under reduced pressure to yield a crude product, which was purified by column chromatography to obtain pure compound 1d as white crystals (35.5%). 1H NMR (CDCl3) δ 7.85-7.82 (m, 1H), 7.48-7.36 (m, 4H), 7.35 (s, 2H), 7.25 (d, 1H, J=4.0 Hz), 6.86 (d, 1H, J=4.2 Hz), 3.96 (s, 3H), 3.95 (s, 6H); MS (ESI) m/z 339.1 (M+H)+.

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate
  3. dry with materialdried with MgSO4
  4. customThe solvent was removed under reduced pressure
  5. customto yield a crude product, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-7740002702bd42a1b853b5e5eacd75b4
Source dataset
uspto-grants-2016_09
Patent number
US09447049B2

Reaction notes

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