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

HRID 746016ノート

反応式

HRID 746016 の反応式
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]

参加物

3

反応物 2

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

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a97ae51448b742cfb578e3b5ae01dd8b
出典データセット
uspto-grants-1986_07
特許番号
US04602027

反応ノート

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