Phosphorus oxychloride → Ethyl 2-chloro-4-(5-chloro-2-thienyl)-5-oxazolebutanoate

HRID 747429ノート

反応式

HRID 747429 の反応式
[Cl:1][C:2]1[S:6][C:5]([C:7]2[NH:8][C:9](=O)[O:10][C:11]=2[CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:23])=O>N1C=CC=CC=1>[Cl:23][C:9]1[O:10][C:11]([CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:7]([C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:8]=1

参加物

4

反応物 2

HCID 24813Phosphorus oxychlorideHCID 18174756Ethyl 4-[4-(5-chloro-2-thienyl)-2-oxo-4-oxazolin-5-yl]butanoate

生成物 1

HCID 12085649Ethyl 2-chloro-4-(5-chloro-2-thienyl)-5-oxazolebutanoate

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
125 °C

実験手順

A mixture of ethyl 4-[4-(5-chloro-2-thienyl)-2-oxo-4-oxazolin-5-yl]butanoate (12.5 g), phosphorus oxychloride (24.5 g) and pyridine (3.16 g) was heated to 120-130° C. and stirred for 45 minutes. The reaction mixture was poured into ice-water (200 ml) and extracted with ethyl acetate (150 ml×2). The organic layer was washed in sequence with a 10% aqueous solution of sodium hydrogen carbonate (100 ml) and a saturated aqueous solution of sodium chloride (100 ml) and dried over anhydrous magnesium sulfate. The organic layer was concentrated, the residue was subjected to silica gel column chromatography, and ethyl 2-chloro-4-(5-chloro-2-thienyl)-5-oxazolebutanoate was obtained as a yellow oil (5.79 g, 48%) from an ethyl acetate-hexane (1:4, v/v)-eluted fraction.

後処理

  1. extractionextracted with ethyl acetate (150 ml×2)
  2. washThe organic layer was washed in sequence with a 10% aqueous solution of sodium hydrogen carbonate (100 ml)
  3. dry with materiala saturated aqueous solution of sodium chloride (100 ml) and dried over anhydrous magnesium sulfate
  4. concentrationThe organic layer was concentrated

出典と根拠

ORDレコード
ord-997f39b5e4864f6c85380d19d258f9c8
出典データセット
uspto-grants-2008_07
特許番号
US07396848B1

反応ノート

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