Ethyl Acetate → Ethyl 2-hydroxy-4-methyl-2-(trifluoromethyl)pent-4-enoate

HRID 430460

반응식

HRID 430460 반응식
[CH2:1](Br)[C:2](=[CH2:4])[CH3:3].[CH2:6]([O:8][C:9](=[O:16])[C:10]([C:12]([F:15])([F:14])[F:13])=[O:11])[CH3:7].[Cl-].[NH4+].C(OCC)(=O)C>O1CCCC1.[Cl-].[Zn+2].[Cl-].[Mn]>[CH2:6]([O:8][C:9](=[O:16])[C:10]([OH:11])([C:12]([F:13])([F:15])[F:14])[CH2:3][C:2](=[CH2:1])[CH3:4])[CH3:7]

참가 물질

8

반응물 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 3577853-Bromo-2-methyl-1-propene2회HCID 2737239Ethyl 3,3,3-trifluoro-2-oxopropanoate

생성물 1

HCID 17935595Ethyl 2-hydroxy-4-methyl-2-(trifluoromethyl)pent-4-enoate

시약·촉매·용매 3

HCID 23930Manganese촉매HCID 3007855Zincchloride촉매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

1.3 g of anhydrous zinc chloride and 13.2 g of granular manganese are heated to boiling in 100 ml of tetrahydrofuran and boiled with 0.2 ml of methallyl bromide for 30 minutes. Then, the solution of 25 g of methallylbromide and 17 g of trifluoropyruvic acid ethyl ester in 80 ml of tetrahydrofuran is added in drops at boiling heat over two hours and boiled for another hour. Then, it is added to saturated ammonium chloride solution and 300 ml of ethyl acetate while being cooled with ice, stirred for 30 minutes at 0° C., and the separated ethyl acetate phase is washed with saturated ammonium chloride solution and three times with water. The solvent is dried (Na2SO4) and concentrated by evaporation, and the residue is distilled in a vacuum. 17.6 g of 2-hydroxy-4-methylene-2-trifluoromethyl-valeric acid ethyl ester, boiling point 48° C., 1 hPa, is obtained.

후처리

  1. temperatureat boiling heat over two hours
  2. waitboiled for another hour
  3. temperaturewhile being cooled with ice
  4. washthe separated ethyl acetate phase is washed with saturated ammonium chloride solution and three times with water
  5. dry with materialThe solvent is dried (Na2SO4)
  6. concentrationconcentrated by evaporation
  7. distillationthe residue is distilled in a vacuum

출처 및 근거

ORD 기록
ord-605ea9751b734934af7fb3bb1d09a996
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06323199B1

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