Sodium hydride → Ethyl 5-methyl-2-heptenoate

HRID 458013Notes

Reaction equation

HRID 458013 reaction equation
[H-].[Na+].C[CH:4]([CH2:8][CH3:9])[CH2:5][CH:6]=[O:7]>CCCCCC.C(COC)OC.COCC>[CH3:4][CH:9]([CH2:5][CH3:6])[CH2:8][CH:4]=[CH:5][C:6]([O:7][CH2:9][CH3:8])=[O:7]

Participants

6

Reactant 2

HCID 24758Sodium hydrideHCID 275233-Methylvaleraldehyde

Product 1

HCID 53937332Ethyl 5-methyl-2-heptenoateYield 122%

Reagents, catalysts & solvents 3

HCID 8058HexaneSolventHCID 80711,2-DimethoxyethaneSolventHCID 10903MethoxyethaneSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60% dispersion, 2.4 g, 65 mmol) was washed with hexane and suspended in dimethoxyethane 60 mL. While cooling in ice water bath triethyl phosphonoacetate was slowly added, calcd. 5 minutes. The reaction was stirred for 15 minutes at 0° C. and a solution of 3-methyl-1-pentanal 11 (6.5 g, 65 mmol) in methoxyethane 20 mL was added. After refluxing overnight, it was concentrated, water and hexane were added, the organic phase was separated, and the aqueous portion discarded. The solution was washed twice with brine and dried on magnesium sulfate. The solvent was evaporated to give 12 (6.75 g, 61%).

Workup

  1. additionwas slowly added
  2. custom5 minutes
  3. temperatureAfter refluxing overnight
  4. concentrationit was concentrated
  5. additionwater and hexane were added
  6. customthe organic phase was separated
  7. washThe solution was washed twice with brine
  8. customdried on magnesium sulfate
  9. customThe solvent was evaporated

Sources & evidence

ORD record
ord-1d07839b13564c738f752134da6013c0
Source dataset
uspto-grants-2007_03
Patent number
US07189747B2

Reaction notes

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