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

HRID 70534ノート

反応式

HRID 70534 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-c1cc47113b6f4fbabb8ccde3e8ec1bb6
出典データセット
uspto-grants-2014_09
特許番号
US08822503B2

反応ノート

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