Sodium Methoxide → HCID 13505582, compound

HRID 1885852Notes

Reaction equation

HRID 1885852 reaction equation
[CH3:1][O-:2].[Na+].Br[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[C:11]([NH:15][C:16]([CH:18]1[CH2:20][C:19]1([CH3:22])[CH3:21])=[O:17])[C:12]([OH:14])=[O:13]>CO>[CH3:21][C:19]1([CH3:22])[CH2:20][CH:18]1[C:16]([NH:15]/[C:11](=[CH:10]\[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][O:2][CH3:1])/[C:12]([OH:14])=[O:13])=[O:17]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 54449392HCID 54449392, compound

Product 1

HCID 13505582HCID 13505582, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2.43 mmoles of sodium methoxide in 5 ml of methanol was added 332 mg (1 mmole) of 8-bromo-2-(2,2-dimethylcyclopropanecarboxamido)-2-octenoic acid. The solution was heated under reflux in a nitrogen atmosphere for 1 hr. The reaction mixture was evaporated under reduced pressure, the residue dissolved in water and acidified with 2.5N hydrochloric acid. The oil which precipitated was extracted with ether (3×). The ether extracts were washed with water, and saturated brine and dried over MgSO4. Removal of the ether under reduced pressure gave a colorless oil that crystallized upon standing. It was recrystallized from ether-hexane to give 140 mg of Z-2-(2,2-dimethylcyclopropanecarboxamido)-8-methoxy-2-octenoic acid, m.p. 71°-72° C. Homogeneous by TLC (toluene-HOAc, 4:1). The NMR spectrum was in accord with the desired structure.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux in a nitrogen atmosphere for 1 hr
  3. customThe reaction mixture was evaporated under reduced pressure
  4. dissolutionthe residue dissolved in water
  5. customThe oil which precipitated
  6. extractionwas extracted with ether (3×)
  7. washThe ether extracts were washed with water, and saturated brine
  8. dry with materialdried over MgSO4
  9. customRemoval of the ether under reduced pressure
  10. customgave a colorless oil that
  11. customcrystallized
  12. customIt was recrystallized from ether-hexane

Sources & evidence

ORD record
ord-414ab08c69f54bd795aea4b7d083b8a8
Source dataset
uspto-grants-1992_09
Patent number
US05147868

Reaction notes

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