Diethyl Oxalate → Ethyl 4-(4-chlorophenyl)-3-methyl-2,4-dioxobutanoate

HRID 1510429노트

반응식

HRID 1510429 반응식
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].O1CCCC1.[CH3:16][CH2:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)=[O:19].[C:27]([O:34][CH2:35][CH3:36])(=[O:33])[C:28]([O:30]CC)=O>C(OCC)C>[Cl:26][C:23]1[CH:22]=[CH:21][C:20]([C:18](=[O:19])[CH:17]([CH3:16])[C:28](=[O:30])[C:27]([O:34][CH2:35][CH3:36])=[O:33])=[CH:25][CH:24]=1

참가 물질

6

반응물 4

HCID 7268Diethyl OxalateHCID 8028TetrahydrofuranHCID 226974'-ChloropropiophenoneHCID 2733832Lithium Hexamethyldisilazide

생성물 1

HCID 5051380Ethyl 4-(4-chlorophenyl)-3-methyl-2,4-dioxobutanoate수율 33.7%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

반응 조건

온도
-78 °C

실험 절차

A 1.0 M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (30 mL, 30 mmol) in anhydrous diethyl ether (120 mL) under argon was cooled to −78° C. in a dry ice/acetone bath. A solution of 4-chloropropiophenone (5.0 g, 29.7 mmol) in anhydrous ether (24 mL) was added dropwise and the mixture was stirred an additional 45 minutes at −78° C. Diethyl oxalate (4.6 mL, 33.9 mmol) was added in one portion; the reaction was warmed to room temperature, and stirred overnight. The light yellow precipitate that formed was collected, washed with ether and dried under vacuum to obtain the lithium enolate of ethyl 4-(4-chlorophenyl)-3-methyl-2,4-dioxobutanoate (2.75 g, 10.0 mmol).

후처리

  1. temperaturethe reaction was warmed to room temperature
  2. stirringstirred overnight
  3. customThe light yellow precipitate that formed
  4. customwas collected
  5. washwashed with ether
  6. customdried under vacuum

출처 및 근거

ORD 기록
ord-3b5cd30040154919a6e1f47720c82fe2
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08211927B2

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