Diketene → HCID 21454932, compound

HRID 435958Notes

Reaction equation

HRID 435958 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.C([O-])(=O)C.[Na+].[CH3:12][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][CH2:15][OH:16]>>[C:4]([O:16][CH2:15][CH2:14][N:13]([CH3:12])[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])(=[O:5])[CH2:3][C:2]([CH3:1])=[O:6]

Participants

4

Reactant 3

HCID 12661DiketeneHCID 517045Sodium AcetateHCID 545700N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanol

Product 1

HCID 21454932HCID 21454932, compound

Conditions

Temperature
50 °C

Procedure

To 84 g. (1.0 mole) of diketene contained in a three-necked round-bottom flask fitted with a mechanical stirrer addition funnel and reflux condenser and heated to 50° C. is added 500 mg. of sodium acetate followed by 175.2 g. (1.0 mole) of N-methyl-N-t-butyloxycarbonylethanolamine over a period of 20-30 minutes. The reaction mixture is allowed to stir at room temperature for 1 hour, after which it is distilled under reduced pressure to provide the desired product, 2-(N-methyl-N-t-butyloxycarbonylamino)ethyl acetoacetate.

Workup

  1. customfitted with a mechanical stirrer addition funnel
  2. temperaturereflux condenser
  3. additionis added 500 mg
  4. distillationafter which it is distilled under reduced pressure

Sources & evidence

ORD record
ord-4b3af576750d43a89f08677e4ef66727
Source dataset
uspto-grants-1977_02
Patent number
US04007184

Reaction notes

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