Potassium Carbonate → HCID 59706513, compound

HRID 1774411Notes

Reaction equation

HRID 1774411 reaction equation
[CH3:1][O:2][C:3](=[O:21])/[C:4](/[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)=[C:5](/[CH:10]([CH3:12])[CH3:11])\[C:6]([O:8][CH3:9])=[O:7].C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][C:30]([O:32][CH3:33])=[O:31].C1(C)C=CC=CC=1.C(OCC)(=O)C>C1(C)C=CC=CC=1.O>[CH3:9][O:8][C:6](=[O:7])/[C:5](/[CH:10]([CH3:11])[CH3:12])=[C:4](/[CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH2:29][C:30]([O:32][CH3:33])=[O:31])=[CH:18][CH:19]=1)\[C:3]([O:2][CH3:1])=[O:21]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 21584019Toluene ethylacetateHCID 59706557HCID 59706557, compound

Product 1

HCID 59706513HCID 59706513, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of 2-(4-hydroxybenzyl)-3-isopropylmaleic acid dimethyl ester (44.1 mg, 0.151 mmol) in (880 μL) were added potassium carbonate (34.7 mg, 0.251 mmol) and methyl bromoacetate (138.4 mg, 0.904 mmol) with stirring at room temperature. After stirring at room temperature for 20 h, the reaction mixture was diluted with toluene and water to separate the phases. The aqueous layer was extracted again with toluene, and the combined organic layer was concentrated under reduced pressure and the residue thus obtained was subjected to silica gel column chromatography (toluene-ethyl acetate 10:1) to give 45.2 mg of the title compound as oil (yield: 82%).

Workup

  1. stirringAfter stirring at room temperature for 20 h
  2. customto separate the phases
  3. extractionThe aqueous layer was extracted again with toluene
  4. concentrationthe combined organic layer was concentrated under reduced pressure
  5. customthe residue thus obtained

Sources & evidence

ORD record
ord-87d6805fd6584f709b55723dde1c7da1
Source dataset
uspto-grants-2016_02
Patent number
US09260375B2

Reaction notes

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