Diethyl Malonate → HCID 15004992, compound

HRID 508276Notes

Reaction equation

HRID 508276 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19]Br)(=[O:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:10]([O:9][C:1](=[O:8])[CH:2]([CH2:19][CH2:18][CH2:17][CH2:16][O:15][C:12](=[O:14])[CH3:13])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH3:11]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 11430Potassium CarbonateHCID 784911-Butanol, 4-bromo-, 1-acetate

Product 1

HCID 15004992HCID 15004992, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 3 was prepared by following a previously reported method.{Santra, 2004 #6} Briefly, diethyl malonate 1 (10 g, 62.5 mmol), 4-bromobutyl acetate 2 (15.84 g, 81.3 mmol) were placed in a round bottom flask containing acetonitrile (120 mL) and stirred for 2 min at room temperature. Then to this, we added potassium carbonate (34.5 g, 250.1 mmol) and refluxed for 36 h. Next, the mixture was filtered and the filtrate was concentrated to obtain a yellow liquid. This was extracted with ethyl acetate, and washed with water. The organic layers were combined and dried over Na2SO4, and purified by column chromatography using 4% ethyl acetate in petroleum ether as the eluent.

Workup

  1. temperaturerefluxed for 36 h
  2. filtrationNext, the mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customto obtain a yellow liquid
  5. extractionThis was extracted with ethyl acetate
  6. washwashed with water
  7. dry with materialdried over Na2SO4
  8. custompurified by column chromatography

Sources & evidence

ORD record
ord-466c1e5a227c429fbbbcb67e01bdc15b
Source dataset
uspto-grants-2015_08
Patent number
US09095611B1

Reaction notes

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