Acetic Acid → 78327-51-2

HRID 2287270Notes

Reaction equation

HRID 2287270 reaction equation
[CH3:1][C:2]1([CH2:7][CH2:8][O:9]C(=O)C)[NH:5][C:4](=[O:6])[CH2:3]1.C[O-].[Na+].C(O)(=O)C>CO>[CH3:1][C:2]1([CH2:7][CH2:8][OH:9])[NH:5][C:4](=[O:6])[CH2:3]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 12874030HCID 12874030, compound

Product 1

HCID 1287403278327-51-2

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Under nitrogen at 0°, a solution of 4-methyl-4-(2-acetoxyethyl)-2-azetidinone (0.014 mole) in 25 ml anhydrous methanol is treated with a solution of sodium methoxide (77 mg, 1.4 mmoles) in 5 ml anhydrous methanol. After stirring for 1 hour, the solution is neutralized with glacial acetic acid. Removal of the methanol in vacuo gives crude 4-methyl-4-(2-hydroxyethyl)-2-azetidinone as an oil. The product is purified by chromatography on silica gel eluting with 10% MeOH/CHCl3 to give the alcohol.

Workup

  1. customRemoval of the methanol in vacuo

Sources & evidence

ORD record
ord-3546d03bc0454bd1a6cb7bd3b6253637
Source dataset
uspto-grants-1981_05
Patent number
US04269873

Reaction notes

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