Benzyl mercaptan → 2-(Benzylthio)-4-methylpyridine

HRID 869741

反応式

HRID 869741 の反応式
[H-].[Na+].[C:3]1([CH2:9][SH:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][N:13]=1>O1CCCC1.O>[CH2:9]([S:10][C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][N:13]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

参加物

6

反応物 3

HCID 7509Benzyl mercaptanHCID 24758Sodium hydrideHCID 27340872-Bromo-4-methylpyridine

生成物 1

HCID 583498362-(Benzylthio)-4-methylpyridine収率 56%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

To a suspension of sodium hydride (60% in oil, 512 mg) in tetrahydrofuran (45 mL) was added dropwise phenylmethanethiol (1.52 g) at room temperature, 2-bromo-4-methylpyridine (2.0 g) was added, and the mixture was stirred at 60° C. for 72 hr. The reaction mixture was diluted with water and extracted twice with ethyl acetate. Combined organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane→hexane-ethyl acetate=24:1) to give the title compound as a brown oil (yield 1.40 g, 56%).

後処理

  1. extractionextracted twice with ethyl acetate
  2. washCombined organic layers were washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent:hexane→hexane-ethyl acetate=24:1)

出典と根拠

ORDレコード
ord-22845b20879149f3b6920dd1312864b0
出典データセット
uspto-grants-2015_03
特許番号
US08969387B2

関連ノート

読み込み中…