Water → HCID 59132627, compound

HRID 1160302Notes

Reaction equation

HRID 1160302 reaction equation
[C:1]([O-:4])([O-])=O.[K+].[K+].[CH3:7][O:8][C:9](=[O:23])[C:10](=[CH:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12].CO[C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Cl)=[CH:28][CH:27]=1.O>CN(C=O)C>[CH3:14][O:13][C:11](=[O:12])[C:10](=[CH:15][C:16]1[CH:17]=[CH:18][C:19]([O:22][CH2:30][C:29]2[CH:32]=[CH:33][CH:26]=[C:27]([O:4][CH3:1])[CH:28]=2)=[CH:20][CH:21]=1)[C:9]([O:8][CH3:7])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 103565Dimethyl ((4-hydroxyphenyl)methylene)malonate

Product 1

HCID 59132627HCID 59132627, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

K2CO3 was added to a solution of 4-hydroxybenzylidene-malonic acid dimethyl ester (6.95 mmol) and 4-methyoxybenzyl chloride (7.64 mmol) in DMF (15 ml). It was stirred at room temperature overnight. The reaction was poured into water, and the product was extracted with ethyl acetate twice. The organic layer was washed with water and saturated brine, dried over Na2SO4, and concentrated in vacuo. The resulting residue was purified using silica gel column chromatography (hexane/ethyl acetate=2/1) to give compound 33.1 as a white solid (3.2 mmol).

Workup

  1. extractionthe product was extracted with ethyl acetate twice
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified

Sources & evidence

ORD record
ord-80cea56e935c4186bf666bff09aec1f2
Source dataset
uspto-grants-2010_10
Patent number
US07816367B2

Reaction notes

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