Sodium Methoxide → HCID 13505582, compound

HRID 1719183Notes

Reaction equation

HRID 1719183 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 2.5 N hydrochloric acid. The oil which precipitated was extracted with ether (3X). 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 (3X)
  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-e17ca1d17672419fb26cc00af4749cba
Source dataset
uspto-grants-1985_09
Patent number
US04539208

Reaction notes

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