Thionyl Chloride → Ethyl 2-[4-(chloromethyl)phenyl]-1,3-oxazole-4-carboxylate

HRID 1716857Notes

Reaction equation

HRID 1716857 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][CH:11]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:13]=2)=[CH:5][CH:4]=1.S(Cl)([Cl:21])=O.N1C2C=CC=CC=2N=N1>C(Cl)Cl.C(Cl)(Cl)Cl>[Cl:21][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][CH:11]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:13]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 46834789Ethyl 2-[4-(hydroxymethyl)phenyl]-1,3-oxazole-4-carboxylateHCID 178418385HCID 178418385, compound

Product 1

HCID 46834790Ethyl 2-[4-(chloromethyl)phenyl]-1,3-oxazole-4-carboxylateYield 82%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of ethyl 2-[4-(hydroxymethyl)phenyl]-1,3-oxazole-4-carboxylate (0.467 g, 1.89 mmol) in CH2Cl2 was treated with a solution of thionyl chloride (0.281 g, 2.36 mmol) and benzotriazole (0.281 g, 2.36 mmol) in CH2Cl2, and stirred 6 hours at room temperature. The reaction was diluted with CHCl3, filtered over Celite and concentrated under vacuum. The resultant residue was purified by flash chromatography (silica, MeOH:CH2Cl2 5%) to give the title product in 82% yield, identified by NMR and mass spectral analyses. LCMS (ESI+) 266 (MH+).

Workup

  1. filtrationfiltered over Celite
  2. concentrationconcentrated under vacuum
  3. customThe resultant residue was purified by flash chromatography (silica, MeOH:CH2Cl2 5%)

Sources & evidence

ORD record
ord-f149aedecfa84eb0a80e0ed0eacee0a5
Source dataset
uspto-grants-2010_09
Patent number
US07803825B2

Reaction notes

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