Ammonia → HCID 19980851, compound

HRID 231347Notes

Reaction equation

HRID 231347 reaction equation
[NH3:1].O=[C:3]([CH3:11])[CH2:4][C:5]([O:7][CH2:8][CH2:9][OH:10])=[O:6]>C(O)C>[NH2:1]/[C:3](/[CH3:11])=[CH:4]\[C:5]([O:7][CH2:8][CH2:9][OH:10])=[O:6]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 118544Butanoic acid, 3-oxo-, 2-hydroxyethyl ester

Product 1

HCID 19980851HCID 19980851, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Anhydrous ammonia gas was bubbled through a solution of 2-hydroxyethyl 3-oxo-butyrate (25 g, 0.17 moles) (ref 5) and ethanol (250 mL) for 20 minutes. This solution was stirred for 16 hours at room temperature. The solvent was removed in vacuo and the resulting oil was chromatographed on silica gel (250 g) using ethyl acetate-hexane 60:40 as eluant. The enriched fractions were combined and the solvent removed in vacuo to give the product; H' NMR CDCl3 4.33 (t, 2H) 3.85 (t, 2H) 3.55 (s, 1H) 2.85 (broad singlet, 1H) 2.31 (s, 3H).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe resulting oil was chromatographed on silica gel (250 g)
  3. customthe solvent removed in vacuo
  4. customto give the product

Sources & evidence

ORD record
ord-de4688cb7e324f85aadd3014ecce9c53
Source dataset
uspto-grants-1989_07
Patent number
US04845225

Reaction notes

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