Sodium Methoxide → HCID 54362627, compound

HRID 259615Notes

Reaction equation

HRID 259615 reaction equation
[CH3:1][O:2][CH2:3][C:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[CH:14][NH:15][C:16]([O:18][CH3:19])=[O:17])=[CH:9][CH:8]=1)=O.[CH3:20][O-:21].[Na+]>CO>[CH3:20][O:21][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][NH:15][C:16]([O:18][CH3:19])=[O:17])[CH:11]=[CH:12][C:7]=1[O:6][CH2:4][CH:3]1[O:2][CH2:1]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 68124141HCID 68124141, compound

Product 1

HCID 54362627HCID 54362627, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
50 °C

Procedure

5.1 g (0.019 mol) of 2-methoxy-4-(2-methoxycarbonylaminovinyl)-acetoxybenzene are suspended in 75 ml of absolute methanol, a solution of 1.04 g (0.019 mol) of sodium methoxide in 15 ml of absolute methanol is added and the mixture is subsequently warmed to 50° C. for 15 minutes. It is then evaporated to dryness in vacuo. The resulting crude sodium salt of 2-methoxy-4-(2-methoxycarbonylaminovinyl)-phenol is heated to the boil, with 20 ml of epichlorohydrin, for 24 hours under a reflux condenser and whilst stirring. Thereafter, the excess epichlorohydrin is removed by distillation under reduced pressure. The residue is partitioned between water and methylene chloride and the organic phase is separated off, dried over sodium sulphate and evaporated. After crystallisation from ether of the crude product thus obtained, 1-[2-methoxy-4-(2-methoxycarbonylaminovinyl)-phenoxy]-2,3-epoxy-propane of melting point 122°-123° C. is obtained.

Workup

  1. customIt is then evaporated to dryness in vacuo
  2. temperatureThe resulting crude sodium salt of 2-methoxy-4-(2-methoxycarbonylaminovinyl)-phenol is heated to the boil, with 20 ml of epichlorohydrin, for 24 hours under a reflux condenser
  3. customThereafter, the excess epichlorohydrin is removed by distillation under reduced pressure
  4. customThe residue is partitioned between water and methylene chloride
  5. customthe organic phase is separated off
  6. dry with materialdried over sodium sulphate
  7. customevaporated
  8. customAfter crystallisation from ether of the crude product
  9. customthus obtained

Sources & evidence

ORD record
ord-19e74d80ce0748878cf1e66e93de2162
Source dataset
uspto-grants-1977_07
Patent number
US04038414

Reaction notes

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