Water → 3-Oxazol-4-yl-acrylic acid ethyl ester

HRID 1096816Notes

Reaction equation

HRID 1096816 reaction equation
[Li]CCCC.[O:6]1[CH:10]=[C:9]([CH:11]=O)[N:8]=[CH:7]1.[OH2:13].[CH3:14][CH2:15][O:16][CH2:17][CH3:18]>>[CH2:15]([O:16][C:17](=[O:13])[CH:18]=[CH:11][C:9]1[N:8]=[CH:7][O:6][CH:10]=1)[CH3:14]

Participants

5

Reactant 4

HCID 962WaterHCID 3283Diethyl Ether3×HCID 142814324-OxazolecarboxaldehydeHCID 178418339Butyllithium

Product 1

HCID 667843523-Oxazol-4-yl-acrylic acid ethyl esterYield 74%

Conditions

Temperature
-78 °C

Procedure

Triethylphosphonoacetate (29.4 mL, 147 mmol) was dissolved in dry Et2O (200 mL) under nitrogen. The sol. was cooled to −78° C., and BuLi (1.6 M in hexane, 85 mL, 136 mmol) was added slowly. The mixture was stirred for 2 h at −78° C., and a sol. of the oxazole-4-carbaldehyde (11.9 g, 122 mmol) in dry Et2O was added slowly. The reaction mixture was stirred for 4 h. The reaction mixture was combined with Et2O and water, and the org. phase was washed with aq. sat. NaHCO3. The org. extracts were dried over MgSO4, filtered and the solvents were carefully removed under reduced pressure (volatile product). Purification of the residue by FC (heptane/EtOAc; 1.5:1→1:1→1:2) yielded the title compound (15.1 g, 74%). LC-MS: tR=0.77, ES+: 209.10.

Workup

  1. stirringThe reaction mixture was stirred for 4 h
  2. washphase was washed with aq. sat. NaHCO3
  3. dry with materialextracts were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were carefully removed under reduced pressure (volatile product)
  6. customPurification of the residue by FC (heptane/EtOAc; 1.5:1→1:1→1:2)

Sources & evidence

ORD record
ord-72c59c4bdb79498da122cfd859472bca
Source dataset
uspto-grants-2012_03
Patent number
US08138340B2

Reaction notes

Loading…