Sodium Methoxide → 5-(3,4-Dimethoxyphenyl)-4,5-dihydro-1,3-oxazol-2-ol

HRID 2052558Notes

Reaction equation

HRID 2052558 reaction equation
C([O:3][C:4](=[O:19])[NH:5][CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)O)C.C[O-].[Na+]>C1(C)C=CC=CC=1>[CH3:18][O:17][C:11]1[CH:10]=[C:9]([CH:7]2[O:19][C:4](=[O:3])[NH:5][CH2:6]2)[CH:14]=[CH:13][C:12]=1[O:15][CH3:16]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 53831097Ethyl (2-(3,4-dimethoxyphenyl)-2-hydroxyethyl)carbamate

Product 1

HCID 30506615-(3,4-Dimethoxyphenyl)-4,5-dihydro-1,3-oxazol-2-olYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3 mmol of 2-(3,4-dimethoxyphenyl)-2-hydroxyethylcarbamic acid ethyl ester is suspended with 4 mmol of sodium methylate in 12 ml. of toluene and heated for 2 hours to a bath temperature of 110° under the exclusion of moisture. During this step, methanol and ethanol are distilled off. The toluene is then withdrawn under vacuum, the residue is taken up in 50 ml. of chloroform and distributed over 10 ml. of water. After drying, filtration, and concentration of the organic phase, the mixture is recrystallized from methanol, thus obtaining an 80% yield of 5-(3,4-dimethoxyphenyl)-2-oxazolidinone, m.p. 114°-117°.

Workup

  1. distillationDuring this step, methanol and ethanol are distilled off
  2. customThe toluene is then withdrawn under vacuum
  3. customAfter drying
  4. filtrationfiltration, and concentration of the organic phase
  5. customthe mixture is recrystallized from methanol

Sources & evidence

ORD record
ord-a45e7795cf214c579e9bf74e8394bc09
Source dataset
uspto-grants-1980_01
Patent number
US04186129

Reaction notes

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