Dimethyl malonate → HCID 10226524, compound

HRID 1797280Notes

Reaction equation

HRID 1797280 reaction equation
[H-].[Na+].[C:3]([O:10][CH3:11])(=[O:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6].Br[CH2:13]/[CH:14]=[CH:15]/[Sn:16]([CH2:25][CH2:26][CH2:27][CH3:28])([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH2:19][CH3:20]>CN(C=O)C>[CH2:25]([Sn:16]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:15]/[CH:14]=[CH:13]/[CH:4]([C:3]([O:10][CH3:11])=[O:9])[C:5]([O:7][CH3:8])=[O:6])[CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 7943Dimethyl malonateHCID 24758Sodium hydrideHCID 10905679167288-95-1

Product 1

HCID 10226524HCID 10226524, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

Sodium hydride (75 mg) was added to a solution of dimethyl malonate (387 mg) in dry DMF (5 mL) at 0° C. [(1E)-3-bromoprop-1-enyl](tributyl)stannane (600 mg) was added to the reaction mixture after 10 min. The reaction mixture was stirred for 3 h at 20° C. and then quenched with saturated NH4Cl(aq.). Extraction with EtOAc and drying (MgSO4) of the organic phase gave, after concentration in vacuo, the crude product. Purification was done by chromatography eluting with petroleum ether/Et2O 12:1 to afford the title compound as a liquid.

Workup

  1. additionwas added to the reaction mixture after 10 min
  2. customquenched with saturated NH4Cl(aq.)
  3. extractionExtraction with EtOAc
  4. dry with materialdrying (MgSO4) of the organic phase
  5. customgave
  6. concentrationafter concentration in vacuo
  7. customPurification
  8. washeluting with petroleum ether/Et2O 12:1

Sources & evidence

ORD record
ord-9fb1341fe3c5408ca196de9ea8b1fa74
Source dataset
uspto-grants-2006_04
Patent number
US07034015B2

Reaction notes

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