Dimethylformamide → HCID 13393784, compound

HRID 2107717Notes

Reaction equation

HRID 2107717 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=O)[CH2:5][CH:6]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[O:7]2.P(Cl)(Cl)([Cl:21])=O.CN(C)[CH:26]=[O:27]>>[Cl:21][C:4]1[C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[OH:1])[O:7][CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:5]=1[CH:26]=[O:27]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 586090HCID 586090, compound

Product 1

HCID 13393784HCID 13393784, compound

Procedure

As in example 1, but using 2.4 g 5-hydroxy-flavanone, 20 ml dimethylformamide and 2.8 ml phosphorous oxychloride. Reaction time is forty hours at 75° C. After hydrolysis and usual work up the residual solid is purified by column chromatography. The best fractions are recrystallised in a mixture of toluene and hexane to give pure yellow crystalline 4-chloro-3-formyl-5-hydroxy-flav-3-ene; m.p. 165° C.

Workup

  1. customReaction time
  2. waitis forty hours at 75° C
  3. customAfter hydrolysis and usual work up the residual solid
  4. customis purified by column chromatography
  5. customThe best fractions are recrystallised in a mixture of toluene and hexane

Sources & evidence

ORD record
ord-b7b8e3059cf34eca93d0f2a0df40fe93
Source dataset
uspto-grants-1990_06
Patent number
US04935441

Reaction notes

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