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

HRID 453852

반응식

HRID 453852 반응식
[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]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 7757Methyl acetoacetateHCID 24758Sodium hydride2회HCID 750161-Chloro-2-fluoro-3-nitrobenzene

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
25 °C

실험 절차

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%

후처리

  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)

출처 및 근거

ORD 기록
ord-2a72ef7018a54390acd9e8b8c1c119fb
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492559B2

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