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Triethylamine → Isopropyl (2Z)-3-hydroxy-2-cyano-4-ethyl-2-hexenoate

HRID 2262444
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HRID 2262444 반응식
[CH2:1]([CH:3]([CH2:7][CH3:8])[C:4](Cl)=[O:5])[CH3:2].[C:9]([CH2:11][C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[O:13])#[N:10].C(N(CC)CC)C>C(Cl)Cl>[OH:5]/[C:4](/[CH:3]([CH2:7][CH3:8])[CH2:1][CH3:2])=[C:11](/[C:9]#[N:10])\[C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[O:13]
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 25917Isopropyl cyanoacetateHCID 759542-Ethylbutyryl chloride

생성물 1

HCID 54693160Isopropyl (2Z)-3-hydroxy-2-cyano-4-ethyl-2-hexenoate수율 68%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

22.2 g (0.16 mol) of 2-ethylbutyryl chloride were added to a solution of 21 g (0.16 mol) of isopropyl cyanoacetate in CH2Cl2, and the reaction mixture was cooled to 0° C. At this temperature, with ice-cooling, 33.5 g (0.33 mol) of triethylamine were added dropwise, and the mixture was then stirred at 25° C. for 2 h. Following subsequent acidic hydrolysis, the organic phase was washed, dried and concentrated. Purification by customary methods gave 24.4 g of the title compound (68% of theory) as a colorless oil (b.p. 70-75° C./1.5 mbar).

후처리

  1. temperatureAt this temperature, with ice-cooling
  2. customacidic hydrolysis
  3. washthe organic phase was washed
  4. customdried
  5. concentrationconcentrated
  6. customPurification by customary methods

출처 및 근거

ORD 기록
ord-461234f4e4274a74b54408507a4eb786
출처 데이터셋
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07851411B2

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