Dimethylformamide → HCID 13393803, compound

HRID 2107729Notes

Reaction equation

HRID 2107729 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C:3](=O)[CH:2]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.P(Cl)(Cl)([Cl:20])=O.CN(C)[CH:25]=[O:26]>>[Cl:20][C:3]1[CH:2]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:1][C:10]2[C:5]([C:4]=1[CH:25]=[O:26])=[CH:6][CH:7]=[CH:8][CH:9]=2

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 123180333-Flavanone

Product 1

HCID 13393803HCID 13393803, compound

Procedure

As in example 1, but using 2.2 g flavan-3-one, 12 ml dimethylformamide and 3 ml phosphorous oxychloride. Reaction time is one hour at 0°-5°. After hydrolysis and usual work up the residual oil is purified by column chromatography. The best fractions give a pale yellow oil of pure 3-chloro-4-formyl-flav-3-ene. TLC (n-hexane/acetone 4:1, SiO2) single spot, Rf =0.47. NMR (90 MHz, CDCl3):δ(ppm)=5.86 [1H, s, H-C(2)]; 6.7-7.5 [3H, m, H-C (6,7,8)]; 7.35 [5H, S,C6H5 ]; 8.15 [1H, dd, H-C(5)].

Workup

  1. customReaction time
  2. customAfter hydrolysis and usual work up the residual oil
  3. customis purified by column chromatography

Sources & evidence

ORD record
ord-d629f6b866914b1491078f343956966e
Source dataset
uspto-grants-1990_06
Patent number
US04935441

Reaction notes

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