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Methyl cyanoacetate → Methyl 2-cyano-4-(2-fluorophenyl)-3-methyl-4-oxobutanoate

HRID 1012374
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HRID 1012374 반응식
[C:1]([CH2:3][C:4]([O:6][CH3:7])=[O:5])#[N:2].C(N(C(C)C)CC)(C)C.Br[CH:18]([CH3:28])[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[F:27])=[O:20]>O1CCCC1>[C:1]([CH:3]([CH:18]([CH3:28])[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[F:27])=[O:20])[C:4]([O:6][CH3:7])=[O:5])#[N:2]
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참가 물질

5

반응물 3

HCID 7747Methyl cyanoacetateHCID 81531DiisopropylethylamineHCID 221113342-Bromo-1-(2-fluorophenyl)propan-1-one

생성물 1

HCID 66924807Methyl 2-cyano-4-(2-fluorophenyl)-3-methyl-4-oxobutanoate수율 80%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
70 °C

실험 절차

To a solution of methyl cyanoacetate (15.5 mL) and diisopropylethylamine (64 mL) in tetrahydrofuran (110 mL) was added a solution of 2-bromo-1-(2-fluorophenyl)propan-1-one (36.8 g) in tetrahydrofuran (160 mL), and the mixture was stirred at 70° C. for 20 hr. The reaction mixture was allowed to cool to room temperature, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=5:1) to give the title compound as a brown oil (yield 31.9 g, 80%).

후처리

  1. temperatureto cool to room temperature
  2. filtrationthe insoluble material was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=5:1)

출처 및 근거

ORD 기록
ord-5f249ae4b6994c4897766bf2f66a4b39
출처 데이터셋
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07977488B2

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