Triethylamine → Ethyl 5-(4-chlorophenyl)oxazole-4-carboxylate

HRID 1506660Notes

Reaction equation

HRID 1506660 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1.[N+:18]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])#[C-:19]>C1COCC1>[Cl:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]2[O:14][CH:19]=[N:18][C:20]=2[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 533707Ethyl isocyanoacetate

Product 1

HCID 2739479Ethyl 5-(4-chlorophenyl)oxazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (20 mL, 144 mmol) was added to a solution of 4-chlorobenzoyl chloride (8.4 g, 48 mmol) in THF (100 mL) at 0° C. Ethyl 2-isocyanoacetate (6.0 g, 53 mmol) was added dropwise and the resulting solution was stirred at room temperature for 1 h. The reaction mixture was partitioned between EtOAc and water. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica column with ethyl acetate and hexanes as eluents to give the desired compound. MS (m/z) 252.1 [M+H]+.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica column with ethyl acetate and hexanes as eluents

Sources & evidence

ORD record
ord-154d0ca150844c3bb7959b249e4d05d0
Source dataset
uspto-grants-2015_12
Patent number
US09220710B2

Reaction notes

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