Water → HCID 13393805, compound

HRID 2107724Notes

Reaction equation

HRID 2107724 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:3]=1[CH:18]=[O:19].[F-:20].[Cs+].O>CN(C)C=O>[F:20][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:3]=1[CH:18]=[O:19]

Participants

5

Reactant 3

HCID 962WaterHCID 25953Cesium fluorideHCID 13393783HCID 13393783, compound

Product 1

HCID 13393805HCID 13393805, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.35 g 4-chloro-3-formyl-flav-3-ene and 7.6 g cesium fluoride in 10 ml dimethylformamide is stirred at 110° C. over 40 minutes. After cooling to room temperature water is added and the solution is extracted with methylene chloride. The organic phase is washed with water, and dried over magnesium sulfate. The solid residue is purified by column chromatography and the best fractions are crystallised in hexane. Pure 4-fluoro-3-formyl-flav-3-ene is obtained as yellow crystals; m.p. 114°-115° C.

Workup

  1. additionis added
  2. extractionthe solution is extracted with methylene chloride
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe solid residue is purified by column chromatography
  6. customthe best fractions are crystallised in hexane

Sources & evidence

ORD record
ord-1a8165c2b878404783c7aa3ca0b864f1
Source dataset
uspto-grants-1990_06
Patent number
US04935441

Reaction notes

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