Triethylamine → Ethyl 3-(4-fluorophenyl)-5-methyl-1,2-oxazole-4-carboxylate

HRID 1625917Notes

Reaction equation

HRID 1625917 reaction equation
[OH:1]/[N:2]=[C:3](\Cl)/[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=1.[C:12]([O:17][CH2:18][CH3:19])(=[O:16])[C:13]#[C:14][CH3:15].C(N(CC)CC)C>C(OCC)C>[CH2:18]([O:17][C:12]([C:13]1[C:3]([C:4]2[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=2)=[N:2][O:1][C:14]=1[CH3:15])=[O:16])[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78043Ethyl 2-butynoateHCID 57063604-Fluoro-N-hydroxybenzimidoyl chloride

Product 1

HCID 22309061Ethyl 3-(4-fluorophenyl)-5-methyl-1,2-oxazole-4-carboxylateYield 61.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of (E)- and/or (Z)—N-hydroxy-4-fluoro-benzenecarboximidoyl chloride (15.4 g, 89 mmol) (11.1 g, 64 mmol) in diethylether (151 mL) was added ethyl 2-butynoate (7.2 g, 7.5 mL, 64 mmol) at 0° C. followed by the dropwise addition of triethylamine (7.8 g, 10.7 mL, 77 mmol) and the resulting mixture allowed to warm up to room temperature overnight. The mixture was then poured onto ice-water, and extracted with diethylether. The combined organic layers were then washed with water and brine, dried over sodium sulfate and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 1:1) afforded the title compound (9.8 g, 44%) which was obtained as an off white solid. MS: m/e=250.1 [M+H]+.

Workup

  1. additionThe mixture was then poured onto ice-water
  2. extractionextracted with diethylether
  3. washThe combined organic layers were then washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 1:1)

Sources & evidence

ORD record
ord-ab5c7907ab094424a40c54660c335830
Source dataset
uspto-grants-2014_07
Patent number
US08785435B2

Reaction notes

Loading…