Dichloromethane → 4-(Chloromethyl)-2-(furan-2-yl)-5-methyl-1,3-oxazole

HRID 1182822Notes

Reaction equation

HRID 1182822 reaction equation
Cl[CH2:2][Cl:3].[O:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9]1[O:10][C:11]([CH3:16])=[C:12](CO)[N:13]=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>O>[Cl:3][CH2:2][C:12]1[N:13]=[C:9]([C:5]2[O:4][CH:8]=[CH:7][CH:6]=2)[O:10][C:11]=1[CH3:16]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chlorideHCID 178612042-(2-Furyl)-5-methyl-4-oxazolylmethanol

Product 1

HCID 223445824-(Chloromethyl)-2-(furan-2-yl)-5-methyl-1,3-oxazoleYield 31%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The dichloromethane (1 mL) solution of {2-(furan-2-yl)-5-methyloxazol-4-yl}methanol (36 mg, 0.2 mmol), N,N-dimethylaminopyridine (37 mg, 0.3 mmol) and p-toluene sulfonyl chloride (57 mg, 0.3 mmol) was stirred at 60° C. for 2 hrs. The reaction mixture was added water and extracted with ethyl acetate. The organic layer was combined, washed with water and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The resulting residues were subjected to silica gel column chromatography (hexane/ethyl acetate) to obtain 4-(chloromethyl)-2-(furan-2-yl)-5-methyloxazole (13 mg, 31%) as a transparent oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7fba429e75f04240aadfd731009a9fdb
Source dataset
uspto-grants-2014_03
Patent number
US08664226B2

Reaction notes

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