Sodium Methoxide → HCID 14217110, compound

HRID 1855692Notes

Reaction equation

HRID 1855692 reaction equation
[CH3:1][O:2][CH2:3][CH:4]=[C:5]1[C:9](=[O:10])[O:8][C:7]([CH3:11])=[N:6]1.[CH3:12][O-:13].[Na+]>CO>[CH3:12][O:13][C:9](=[O:10])/[C:5](/[NH:6][C:7](=[O:8])[CH3:11])=[CH:4]/[CH2:3][O:2][CH3:1]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 54228403HCID 54228403, compound

Product 1

HCID 14217110HCID 14217110, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution consisting of 19 g (0.165 mol) of oxazolones 3 and 100 ml of methanol was treated with solid sodium methoxide until the reaction mixture was slightly basic (pH 9 as indicated by moist pH paper). The solution was stirred for 3/4 hr. at room temperature. The reaction mixture was concentrated in vacuo, and the residue taken up in 500 ml of ether. Petroleum ether (bp 35°-60°) was added until the solution was slightly turbid. An additional portion of ether was added to clear the turbidity and the resultant solution was treated with charcoal and filtered through Celite®. The solvents were removed in vacuo, and the residue dried at 0.1 mm. Crystallization from ether/petroleum ether (bp 35°-60°) yielded Z-2-acetamido-4-methoxy-2-butenoic acid methyl ester (4): mp 60°-61°; IR (CHCl3) 3415, 1720, 1700, 1500 cm-1 ; UV (EtOH) λmax 226 nm (ε7500); NMR (CDCl3) δ 7.5 (broad, 1H, NH), 6.7 (t, 1H, --CH2CH=), 4.1 (d, 2H, --CH2CH=), 3.8 (s, 3H, CH3O2C--), 3.4 (s, 3H, CH3OCH2 --), 2.14 (s, 3H, CH3CONH--). (Calcd. for C8H13NO4 : C, 51.33; H, 7.00; N, 7.48. Found: C, 51.20; H, 7.13; N, 7.69.)

Workup

  1. customat room temperature
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionPetroleum ether (bp 35°-60°) was added until the solution
  4. additionAn additional portion of ether was added
  5. additionthe resultant solution was treated with charcoal
  6. filtrationfiltered through Celite®
  7. customThe solvents were removed in vacuo
  8. customthe residue dried at 0.1 mm
  9. customCrystallization from ether/petroleum ether (bp 35°-60°)

Sources & evidence

ORD record
ord-a24a0233a64c467592256dffb21a496e
Source dataset
uspto-grants-1980_08
Patent number
US04216008

Reaction notes

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