2-Oxobutanoic Acid → HCID 11041594, compound

HRID 906847Notes

Reaction equation

HRID 906847 reaction equation
[O:1]=[C:2]([CH2:6][CH3:7])[C:3]([OH:5])=[O:4].[CH2:8](O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O>C1C=CC=CC=1>[CH2:8]([O:4][C:3](=[O:5])[C:2](=[O:1])[CH2:6][CH3:7])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 582-Oxobutanoic AcidHCID 244Benzyl AlcoholHCID 962Water2×

Product 1

HCID 11041594HCID 11041594, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2-oxobutyric acid (11.5 g, 113 mmol), and benzyl alcohol (14.0 mL, 135 mmol) in benzene (100 mL) was heated to reflux under a Dean-Stark water separator. After refluxing for 16 hrs˜2 mL of water had collected in the trap (˜100% of theoretical). The reaction mixture was allowed to cool to ambient temperature, and then concentrated under reduced pressure to afford a pale yellow oil. The crude material was purified by flash chromatography eluting with a gradient from 0% to 15% ethyl acetate/hexane to afford 2-oxo-butyric acid benzyl ester (13.0 g, 60% yield) as a clear colorless oil. 1H-NMR (400 MHz, CDCl3): δ 7.42-7.35 (5H, m), 5.28 (5H, s), 2.87 (2H, q, J=7.2 Hz), 1.12 (3H, t, J=7.2 Hz).

Workup

  1. temperaturewas heated
  2. customhad collected in the trap (˜100% of theoretical)
  3. concentrationconcentrated under reduced pressure
  4. customto afford a pale yellow oil
  5. customThe crude material was purified by flash chromatography
  6. washeluting with a gradient from 0% to 15% ethyl acetate/hexane

Sources & evidence

ORD record
ord-584860fd488946f591a2b76c01a0c212
Source dataset
uspto-grants-2011_09
Patent number
US08013001B2

Reaction notes

Loading…