Ethyl (2Z)-2-methoxyimino-3-oxo-butanoate → Ethyl 2-methoxyimino-3-t-butoxycarbonylhydrazonobutyrate

HRID 434876Notes

Reaction equation

HRID 434876 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:10]([CH3:12])=O)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:13]([O:17][C:18]([NH:20][NH2:21])=[O:19])([CH3:16])([CH3:15])[CH3:14]>C(O)C>[CH3:1][O:2][N:3]=[C:4]([C:10](=[N:21][NH:20][C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19])[CH3:12])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 43493Ethyl (2Z)-2-methoxyimino-3-oxo-butanoateHCID 70091tert-Butyl carbazate

Product 1

HCID 54569379Ethyl 2-methoxyimino-3-t-butoxycarbonylhydrazonobutyrate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 2-methoxyiminoacetoacetate (a mixture of syn and anti isomers) (34.6 g.) and t-butoxycarbonylhydrazine (26.4 g.) in ethanol (200 ml.) was stirred for 7.5 hours at ambient temperature and allowed to stand overnight to precipitate crystals. The crystals were collected by filtration, washed with ethanol and dried to give ethyl 2-methoxyimino-3-t-butoxycarbonylhydrazonobutyrate (a mixture of syn and anti isomers) (41.7 g.), mp 144° to 145° C.

Workup

  1. waitto stand overnight
  2. customto precipitate crystals
  3. filtrationThe crystals were collected by filtration
  4. washwashed with ethanol
  5. customdried

Sources & evidence

ORD record
ord-43ea0ba2aa0f4e66994064a43a20b218
Source dataset
uspto-grants-1983_08
Patent number
US04399133

Reaction notes

Loading…