Thionyl Chloride → 4-(Chloromethyl)-5-methyl-2-(2-phenylethenyl)-1,3-oxazole

HRID 746016Notes

Reaction equation

HRID 746016 reaction equation
O[CH2:2][C:3]1[N:4]=[C:5]([CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:6][C:7]=1[CH3:8].S(Cl)([Cl:19])=O>>[Cl:19][CH2:2][C:3]1[N:4]=[C:5]([CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:6][C:7]=1[CH3:8]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 54521586[5-Methyl-2-(2-phenylethenyl)-1,3-oxazol-4-yl]methanol

Product 1

HCID 542375204-(Chloromethyl)-5-methyl-2-(2-phenylethenyl)-1,3-oxazole

Procedure

4-Hydroxymethyl-5-methyl-2-styryloxazole (1.0 g) was added to thionyl chloride (3 ml) and the mixture was allowed to stand at room temperature for 30 minutes. The thionyl chloride was distilled off under reduced pressure. The residue was neutralized with aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was then distilled off and isopropyl ether was added to the residue to give 4-chloromethyl-5-methyl-2-styryloxazole as crystals; yield 0.98 g (90.7%). Recrystallization from ether gave light-yellow plates melting at 108°-109° C.

Workup

  1. distillationThe thionyl chloride was distilled off under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was then distilled off
  6. additionisopropyl ether was added to the residue

Sources & evidence

ORD record
ord-a97ae51448b742cfb578e3b5ae01dd8b
Source dataset
uspto-grants-1986_07
Patent number
US04602027

Reaction notes

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