Hydrochloric Acid → (E)-Methyl 2-(2-chloro-6-nitrophenyl)-3-hydroxybut-2-enoate

HRID 453852

反応式

HRID 453852 の反応式
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].F[C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=1[N+:19]([O-:21])=[O:20].Cl>CN(C=O)C.O>[Cl:18][C:17]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:19]([O-:21])=[O:20])[C:12]=1/[C:2](=[C:3](\[OH:4])/[CH3:5])/[C:1]([O:7][CH3:8])=[O:6]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 7757Methyl acetoacetateHCID 24758Sodium hydride2 回HCID 750161-Chloro-2-fluoro-3-nitrobenzene

生成物 1

HCID 86761957(E)-Methyl 2-(2-chloro-6-nitrophenyl)-3-hydroxybut-2-enoate収率 51%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
25 °C

実験手順

Methyl acetoacetate (59.82 mmol, 2.1 equiv.) was added dropwise at 0° C. to a suspension of NaH (65.52 mmol, 2.3 equiv.) in DMF (40 ml). Then the mixture was stirred for 10 min and subsequently heated to 25° C. 2-Fluoro-3-chloronitrobenzene (28.49 mmol, 1.0 equiv.) was cooled with an ice bath in a reaction flask, and the NaH suspension was added. Then stirring was carried out for 16 h at 25° C. 2 M HCl (5 ml) and water (10 ml) were then added, and extraction with diethyl ether (3×20 ml) was carried out. The combined organic phases were washed with water (10 ml) and sat. NaCl solution (20 ml), dried over Na2SO4 and reduced under reduced pressure. The residue was purified by column chromatography (5% ethyl acetate in hexane). Yield: 51%

後処理

  1. stirringThen stirring
  2. waitwas carried out for 16 h at 25° C
  3. extractionextraction with diethyl ether (3×20 ml)
  4. washThe combined organic phases were washed with water (10 ml) and sat. NaCl solution (20 ml)
  5. dry with materialdried over Na2SO4
  6. customThe residue was purified by column chromatography (5% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-2a72ef7018a54390acd9e8b8c1c119fb
出典データセット
uspto-grants-2013_07
特許番号
US08492559B2

関連ノート

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