Dimethylformamide → HCID 13393792, compound

HRID 2107722Notes

Reaction equation

HRID 2107722 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[C:11]([O:15][CH3:16])[CH:10]=[C:9]2[C:4]=1[C:5](=O)[CH2:6][CH:7]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[O:8]2.P(Cl)(Cl)([Cl:26])=O.CN(C)[CH:31]=[O:32]>>[Cl:26][C:5]1[C:4]2[C:9](=[CH:10][C:11]([O:15][CH3:16])=[C:12]([O:13][CH3:14])[C:3]=2[O:2][CH3:1])[O:8][CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:6]=1[CH:31]=[O:32]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 124051375,6,7-Trimethoxy-2-phenyl-2,3-dihydro-4H-1-benzopyran-4-one

Product 1

HCID 13393792HCID 13393792, compound

Procedure

As in example 1, but using 15 g 5,6,7-trimethoxyflavanone, 150 ml dimethylformamide and 26 ml phosphorous oxychloride. Reaction time is forty eight hours at room temperature. After hydrolysis and usual work up, the residual solid is purified by preparative HPLC and the best fractions are crystallised in hexane. 4-chloro-3-formyl-5,6,7-trimethoxyflav-3-ene is obtained as yellow crystals; m.p. 84°-87° C.

Workup

  1. customReaction time
  2. waitis forty eight hours at room temperature
  3. customAfter hydrolysis and usual work up
  4. customthe residual solid is purified by preparative HPLC
  5. customthe best fractions are crystallised in hexane

Sources & evidence

ORD record
ord-3f2c4f1dea9a4de7846c1472f60509c2
Source dataset
uspto-grants-1990_06
Patent number
US04935441

Reaction notes

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