Phenol → HCID 54504686, compound

HRID 1492927Notes

Reaction equation

HRID 1492927 reaction equation
Br[CH2:2][C:3]1[CH:19]=[CH:18][C:6]2[S:7][CH:8]=[C:9]([C:10](=[CH:15][O:16][CH3:17])[C:11]([O:13][CH3:14])=[O:12])[C:5]=2[CH:4]=1.[C:20]1([OH:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:26]([CH2:2][C:3]1[CH:19]=[CH:18][C:6]2[S:7][CH:8]=[C:9]([C:10](=[CH:15][O:16][CH3:17])[C:11]([O:13][CH3:14])=[O:12])[C:5]=2[CH:4]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 53960446HCID 53960446, compound

Product 1

HCID 54504686HCID 54504686, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1 g of methyl α-(5-bromomethyl-3-benzo[b]-thienyl)-β-methoxyacrylate (see Example 11 ), 0.28 g of phenol and 2 g of potassium carbonate in 20 ml of dimethylformamide is heated for 2 hours at 50° C. The mixture is cooled to room temperature and filtered, and the filtrate is then concentrated under reduced pressure, and the crude product is purified by chromatography on silica gel using diethyl ether/n-hexane (1:1). Recrystallization from methylene chloride/n-hexane gives methyl α-(5-phenoxymethyl-3-benzo[b]thienyl)-β-methoxyacrylate as colourless crystals, m.p. 130° C.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. filtrationfiltered
  3. concentrationthe filtrate is then concentrated under reduced pressure
  4. customthe crude product is purified by chromatography on silica gel
  5. customRecrystallization from methylene chloride/n-hexane

Sources & evidence

ORD record
ord-3320ffe4bd57491dbbabaab430c42aeb
Source dataset
uspto-grants-1994_12
Patent number
US05376677

Reaction notes

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