Acetone → HCID 19910737, compound

HRID 1607290Notes

Reaction equation

HRID 1607290 reaction equation
[OH:1][C:2]1[C:7]2[C:8]([CH3:20])=[C:9]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[O:10][C:6]=2[C:5]([Cl:21])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:28][C:29]([CH3:31])=O>>[CH2:31]([O:1][C:2]1[C:7]2[C:8]([CH3:20])=[C:9]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[O:10][C:6]=2[C:5]([Cl:21])=[CH:4][CH:3]=1)[CH:29]=[CH2:28]

Participants

4

Reactant 3

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 14570900HCID 14570900, compound

Product 1

HCID 19910737HCID 19910737, compound

Procedure

To a solution of 4-hydroxy-7-chloro-2-(4'-methoxyphenylmethyl)-3-methylbenzofuran (164) (Example 44) (1.5 g, 5 mmol) in 30 mL acetone was added potassium carbonate (690 mg, 5 mmol) amd allyl bromide (605 mg, 5 mmol). The mixture was refluxed for 20 h, then filtered through celite after cooling to room temperature. Concentration of the filtrate gave 1.94 g of the 4-allyloxy-7-chloro-2-(4'-methoxyphenylmethyl)-3-methylbenzofuran as a light brown oil. The crude material was refluxed in 8 mL o-dichlorobenzene for 6 h. Evaporation of the solvent followed by chromatography gave the title compound as a white solid, mp 90°-93° C.

Workup

  1. temperatureThe mixture was refluxed for 20 h
  2. filtrationfiltered through celite

Sources & evidence

ORD record
ord-75762963f6c943a5905f9833f69c226c
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

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