2,3-Dichloropropene → Ethyl 4-chloro-2,2-dimethylpent-4-enoate

HRID 1975731노트

반응식

HRID 1975731 반응식
C(N[CH:5]([CH3:7])[CH3:6])(C)C.C([Li])CCC.[C:13]([O:18][CH2:19][CH3:20])(=[O:17])[CH:14]([CH3:16])[CH3:15].[Cl:21]C(CCl)=C>C1COCC1>[Cl:21][C:5](=[CH2:6])[CH2:7][C:14]([CH3:16])([CH3:15])[C:13]([O:18][CH2:19][CH3:20])=[O:17]

참가 물질

6

반응물 4

HCID 65652,3-DichloropropeneHCID 7342Ethyl isobutyrateHCID 7912DiisopropylamineHCID 178418339Butyllithium

생성물 1

HCID 3653118Ethyl 4-chloro-2,2-dimethylpent-4-enoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of diisopropylamine (126.5 g; 1.25 mol) in 1500 mL THF at -78° C. was added n-butyllithium (500 mL of a 2.5M solution in hexanes). Upon completion of addition, the mixture was stirred for 30 minutes. A solution of ethyl isobutyrate (132 g; 1.14 mol) in 300 mL THF was added slowly over about 1 hour. The reaction was then allowed to stir for an additional hour at -78° C. 2,3-Dichloro-1-propene (138.7 g; 1.25 mol) was added dropwise. The cooling bath was removed and the reaction was stirred at ambient temperature for 15 hours. Saturated aqueous ammonium chloride solution was added and the THF was removed in vacuo. The aqueous residue was then extracted with ethyl acetate. The extracts were dried over magnesium sulfate and concentrated. Distillation yielded ethyl 4-chloro-2,2-dimethyl-4-pentenoate as a colorless liquid (b.p. 100°-104° C./30 torr).

후처리

  1. additionUpon completion of addition
  2. stirringto stir for an additional hour at -78° C
  3. customThe cooling bath was removed
  4. stirringthe reaction was stirred at ambient temperature for 15 hours
  5. additionSaturated aqueous ammonium chloride solution was added
  6. customthe THF was removed in vacuo
  7. extractionThe aqueous residue was then extracted with ethyl acetate
  8. dry with materialThe extracts were dried over magnesium sulfate
  9. concentrationconcentrated
  10. distillationDistillation

출처 및 근거

ORD 기록
ord-4e2f8cf2b12a4610bfcf22f7aaf98422
출처 데이터셋
uspto-grants-1994_02
특허 번호
US05288743

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