Water → (3E)-4-(4-tert-Butylphenyl)-4-(5-chloro-6-methoxypyridin-2-yl)but-3-enenitrile

HRID 70534노트

반응식

HRID 70534 반응식
[C-:1]#[N:2].[Na+].Br[CH2:5]/[CH:6]=[C:7](/[C:18]1[N:23]=[C:22]([O:24][CH3:25])[C:21]([Cl:26])=[CH:20][CH:19]=1)\[C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:10][CH:9]=1.O>C(O)C>[C:14]([C:11]1[CH:12]=[CH:13][C:8](/[C:7](/[C:18]2[CH:19]=[CH:20][C:21]([Cl:26])=[C:22]([O:24][CH3:25])[N:23]=2)=[CH:6]\[CH2:5][C:1]#[N:2])=[CH:9][CH:10]=1)([CH3:17])([CH3:16])[CH3:15]

참가 물질

5

반응물 3

HCID 962WaterHCID 8929Sodium CyanideHCID 584528146-[(1E)-3-Bromo-1-(4-tert-butylphenyl)prop-1-en-1-yl]-3-chloro-2-methoxypyridine

생성물 1

HCID 58452831(3E)-4-(4-tert-Butylphenyl)-4-(5-chloro-6-methoxypyridin-2-yl)but-3-enenitrile수율 53.3%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Sodium cyanide (137 mg) was added to a solution of 6-[(1E)-3-bromo-1-(4-tert-butylphenyl)prop-1-en-1-yl]-3-chloro-2-methoxypyridine (500 mg) in ethanol (10 mL), and the mixture was stirred at room temperature for 22 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with a 2 M sodium hydroxide solution and brine, dried over sodium sulfate and filtered, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1→4:1) to give the title compound as a yellow oil (230 mg, 53%).

후처리

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with a 2 M sodium hydroxide solution and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customafter which the solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1→4:1)

출처 및 근거

ORD 기록
ord-c1cc47113b6f4fbabb8ccde3e8ec1bb6
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822503B2

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