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

HRID 548919

Reaction equation

HRID 548919 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.CN([CH:15]=[CH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])C.C(N(CC)CC)C>C(OCC)C>[CH2:20]([O:19][C:17]([C:16]1[C:3]([C:4]2[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=2)=[N:2][O:1][CH:15]=1)=[O:18])[CH3:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 121015Ethyl 3-(N,N-dimethylamino)acrylateHCID 57063604-Fluoro-N-hydroxybenzimidoyl chloride

Product 1

HCID 743179Ethyl 3-(4-fluorophenyl)-1,2-oxazole-4-carboxylateYield 88.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of (E)- and/or (Z)-N-hydroxy-4-fluoro-benzenecarboximidoyl chloride (50 g, 241 mmol) in diethylether (1 L) was added a solution of ethyl 3-(N,N-dimethylamino)acrylate (87 mL, 601 mmol) and triethylamine (49 mL, 349 mmol) in diethylether (1 L). The resulting mixture was then stirred for 14 h at room temperature and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 4:1) afforded the title product (50.2 g, 88%) which was obtained as a light yellow solid. MS: m/e=236.1 [M+H]+.

Workup

  1. customevaporated
  2. customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 4:1)

Sources & evidence

ORD record
ord-b27a4707bb60451c964b72ec626a074e
Source dataset
uspto-grants-2011_05
Patent number
US07943619B2

Linked notes

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