Dimethylformamide → 3-(3,4-Dimethoxy-phenyl)-6-ethyl-7-hydroxy-chromen-4-one

HRID 1296877Notes

Reaction equation

HRID 1296877 reaction equation
[CH2:1]([C:3]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:4]=1O)[CH3:2].[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH2:21][C:22]([OH:24])=O)[CH:16]=[CH:17][C:18]=1[O:19][CH3:20].P(Cl)(Cl)(Cl)(Cl)Cl.CN([CH:34]=[O:35])C>>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([C:21]2[C:22](=[O:24])[C:6]3[C:7](=[CH:8][C:9]([OH:10])=[C:3]([CH2:1][CH3:2])[CH:4]=3)[O:35][CH:34]=2)[CH:16]=[CH:17][C:18]=1[O:19][CH3:20]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7139(3,4-Dimethoxyphenyl)acetic acidHCID 24819Phosphorus pentachlorideHCID 98339742-Ethylresorcinol

Product 1

HCID 589135643-(3,4-Dimethoxy-phenyl)-6-ethyl-7-hydroxy-chromen-4-oneYield 92%

Procedure

This compounds was synthesised in the same manner as described above. Ethyl resorcinol (0.83 g, 6 mmol), 3,4-dimethoxyphenylacetic acid (0.83 g, 6 mmol), BF3Et2O (4 ml), PCl5 (1.9 g, 9.1 mmol), DMF (5 ml and 10 ml). The precipitate formed was filtered and re-crystallized from methanol to give 3-(3,4-dimethoxy-phenyl)-6-ethyl-7-hydroxy-chromen-4-one as a pale brown solid (1.8 g, 92%); Rf 0.4 cf SM 0.5 ether/petroleum ether [40–60° C.] (50/50).

Workup

  1. customThis compounds was synthesised in the same manner
  2. customThe precipitate formed
  3. filtrationwas filtered
  4. customre-crystallized from methanol

Sources & evidence

ORD record
ord-a258c6612f3240f38d55d360c5ab1441
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

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