Phenacyl bromide → HCID 1794747, compound

HRID 557152Notes

Reaction equation

HRID 557152 reaction equation
[C:1]([C:9]1[C:10]([OH:21])=[CH:11][CH:12]=[C:13]2[C:18]=1[O:17][C:16](=[O:19])[CH:15]=[C:14]2[CH3:20])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:23][C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:25].C([O-])([O-])=O.[K+].[K+]>CC#N>[C:24]([C:23]1[O:21][C:10]2=[CH:11][CH:12]=[C:13]3[C:18]([O:17][C:16](=[O:19])[CH:15]=[C:14]3[CH3:20])=[C:9]2[C:1]=1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:25])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 11430Potassium CarbonateHCID 5378080HCID 5378080, compound

Product 1

HCID 1794747HCID 1794747, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The route shown in Scheme 1 exemplifies synthesis of the coumarin compounds of the present invention. Triethylamine is added to a solution of 7-hydroxy-4-methyl-chromen-2-one (i) and a benzoyl chloride (ii) in THF at room temperature. The reaction mixture is stirred at room temperature overnight and filtered. The filtrate is concentrated to afford a 7-benzoyloxy-4-methyl-coumarin (iii). A mixture of compound (iii) and finely powdered aluminum chloride is heated at 170° C. for 2 hours to afford an 8-benzoyl-7-hydroxy-4-methyl-chromen-2-one (iv). A mixture of compound (iv), 2-bromoacetophenone (v), and K2CO3 in CH3CN is refluxed overnight. The reaction mixture is filtered and the filtrate is concentrated. The residue is purified by column chromatography to afford a pure 8-benzoyl-4-methyl-9-phenyl-furo[2,3-h]chromen-2-one (vi).

Workup

  1. temperatureis refluxed overnight
  2. filtrationThe reaction mixture is filtered
  3. concentrationthe filtrate is concentrated
  4. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-1ea80862adfd49f1acdfe0bf050273c0
Source dataset
uspto-grants-2011_11
Patent number
US08058427B2

Reaction notes

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