Thionyl Chloride → 4-[(4-Chloromethyl-2-methoxyphenoxy)methyl]-2-(2-furyl)-1,3-oxazole

HRID 2221571ノート

反応式

HRID 2221571 の反応式
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][CH:8]=[C:9]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19]O)=[CH:15][C:14]=2[O:21][CH3:22])[N:10]=1.S(Cl)([Cl:25])=O>>[Cl:25][CH2:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][CH2:11][C:9]2[N:10]=[C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)[O:7][CH:8]=2)=[C:14]([O:21][CH3:22])[CH:15]=1

参加物

3

反応物 2

HCID 24386Thionyl ChlorideHCID 69215267(4-([2-(2-Furyl)-1,3-oxazol-4-yl]methoxy)-3-methoxyphenyl)methanol

生成物 1

HCID 230763434-[(4-Chloromethyl-2-methoxyphenoxy)methyl]-2-(2-furyl)-1,3-oxazole収率 74%

実験手順

(4-([2-(2-Furyl)-1,3-oxazol-4-yl]methoxy)-3-methoxyphenyl)methanol (5.0 g) was added to thionyl chloride (5 mL) at 0° C., and the mixture was stirred at room temperature for 30 min. The reaction mixture was concentrated and ethyl acetate was added to the residue. The ethyl acetate layer was washed successively with saturated aqueous sodium hydrogen carbonate, saturated brine, dried over anhydrous magnesium sulfate and concentrated to give 4-[(4-chloromethyl-2-methoxyphenoxy)methyl]-2-(2-furyl)-1,3-oxazole as pale-brown crystals (3.95 g, yield 74%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 123-124° C.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. additionethyl acetate was added to the residue
  3. washThe ethyl acetate layer was washed successively with saturated aqueous sodium hydrogen carbonate, saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-896bb66f1413436bb18ce9d6b95f8610
出典データセット
uspto-grants-2008_05
特許番号
US07368578B2

反応ノート

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