Dimethyl malonate → HCID 67239285, compound

HRID 521489Notes

Reaction equation

HRID 521489 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:14])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9](Br)[CH:8]=1.[C:15]([O:22][CH3:23])(=[O:21])[CH2:16][C:17]([O:19][CH3:20])=[O:18]>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C>[CH3:20][O:19][C:17](=[O:18])[CH:16]([C:11]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:6][C:5]([O:4][CH3:3])=[O:14])[CH:12]=1)[C:15]([O:22][CH3:23])=[O:21]

Participants

7

Reactant 3

HCID 7943Dimethyl malonateHCID 24758Sodium hydrideHCID 11746402Methyl 2-(3-bromophenyl)acetate

Product 1

HCID 67239285HCID 67239285, compoundYield 44.3%

Reagents, catalysts & solvents 3

HCID 2734635Tri-tert-butylphosphine tetrafluoroborateCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Tris(dibenzylideneacetone)dipalladium(0) (0.104 g, 0.113 mmol), tri-(tert-butyl)phosphonium tetrafluoroborate (65.8 mg, 0.227 mmol) and sodium hydride (295 mg, 60% dispersion in mineral oil) were charged into a flask under an argon atmosphere. (3-Bromophenyl)acetic acid methyl ester (1.30 g, 5.67 mmol) was dissolved in THF (10 ml) and added to the mixture. Subsequently, dimethyl malonate (0.995 g, 7.37 mmol) was added and the mixture stirred under reflux overnight. The mixture was filtered over a small plug of silica gel, evaporated to dryness and the residue purified by silica gel chromatography (HEP/EA gradient) to yield 0.704 g of the title compound.

Workup

  1. additionadded to the mixture
  2. temperatureunder reflux overnight
  3. filtrationThe mixture was filtered over a small plug of silica gel
  4. customevaporated to dryness
  5. customthe residue purified by silica gel chromatography (HEP/EA gradient)

Sources & evidence

ORD record
ord-6685e20ebfe74a9fa182e79f0c92a14d
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Reaction notes

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