Water → Ethyl 2-methyl-4,4,4-trifluoroacetoacetate

HRID 366927

반응식

HRID 366927 반응식
[O:1]=[C:2]([C:9]([F:12])([F:11])[F:10])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:13]I.[Cl-].[NH4+].O>C(COC)OC.[Cl-].[Na+].O>[O:1]=[C:2]([C:9]([F:10])([F:11])[F:12])[CH:3]([CH3:13])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

참가 물질

7

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 67793Ethyl 4,4,4-trifluoroacetoacetate

생성물 1

HCID 2737204Ethyl 2-methyl-4,4,4-trifluoroacetoacetate

시약·촉매·용매 2

HCID 80711,2-Dimethoxyethane용매HCID 57417360Sodium chloride; water용매

실험 절차

Sodium hydride (7.05 g of a 50% oil dispersion, 0.15 mol) was washed 3 times with 25 ml of dimethoxyethane to remove the oil and then suspended in 220 ml of dimethoxyethane, under an argon atmosphere and cooled in an ice bath. A solution of ethyl 3-keto-4,4,4-trifluorobutanoate (25.77 g, 0.14 mol) in 25 ml of dimethoxyethane was added dropwise from an addition funnel to the stirred suspension. After the addition was completed, the cooling bath was removed and the reaction mixture stirred for 30 minutes past the cessation of hydrogen gas evolution. Methyl iodide (43.0 ml, 0.70 mole) was added by syringe and the reaction mixture refluxed overnight. The reaction was cooled to room temperature and poured into a separatory funnel containing a 1:1:1 mixture of saturated ammonium chloride:brine:water. The layers were separated and the aqueous phase extracted with 100 ml ether. The combined organic phase and ether extract was washed with brine, dried over magnesium sulfate and filtered. The solvents were removed by distillation at atmospheric pressure using a Vigreaux column leaving ethyl 3-keto-2-methyl-4,4,4-trifluorobutanoate as the pot residue. Rf: (EtAc/hexane--20:80)

후처리

  1. washSodium hydride (7.05 g of a 50% oil dispersion, 0.15 mol) was washed 3 times with 25 ml of dimethoxyethane
  2. customto remove the oil
  3. temperaturecooled in an ice bath
  4. additionAfter the addition
  5. customthe cooling bath was removed
  6. temperaturethe reaction mixture refluxed overnight
  7. additionpoured into a separatory funnel
  8. additioncontaining
  9. customThe layers were separated
  10. extractionthe aqueous phase extracted with 100 ml ether
  11. extractionThe combined organic phase and ether extract
  12. washwas washed with brine
  13. dry with materialdried over magnesium sulfate
  14. filtrationfiltered
  15. customThe solvents were removed by distillation at atmospheric pressure

출처 및 근거

ORD 기록
ord-8b38f0d4a0884ecab3785df05befd069
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06130315

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