1,2,3,6-Tetrahydro-4-phenylpyridine → 4-(3,6-Dihydro-4-phenyl-1(2H)-pyridinyl)-1-butyne

HRID 128948ノート

反応式

HRID 128948 の反応式
S(C1C=CC(C)=CC=1)(O[CH2:5][CH2:6][C:7]#[CH:8])(=O)=O.[C:16]1([C:22]2[CH2:23][CH2:24][NH:25][CH2:26][CH:27]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[C:16]1([C:22]2[CH2:27][CH2:26][N:25]([CH2:8][CH2:7][C:6]#[CH:5])[CH2:24][CH:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

5

反応物 3

HCID 825531,2,3,6-Tetrahydro-4-phenylpyridineHCID 2720203-Butynyl p-toluenesulfonateHCID 516892Sodium Bicarbonate

生成物 1

HCID 107985574-(3,6-Dihydro-4-phenyl-1(2H)-pyridinyl)-1-butyne

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 3-butynyl tosylate (25.0 g, 0.11 mol), 4-phenyl-1,2,3,6-tetrahydropyridine (21.8 g, 0.11 mol) and sodium bicarbonate (10.3 g, 0.12 mol) in 300 mL of dimethylformamide is heated at 80° C. for 18 hours. The solvent is removed under reduced pressure, and the residue is partitioned between 200 mL of dichloromethane and 200 mL of water. The aqueous layer is extracted with 100 mL of dichloromethane and the combined organic layers are dried (sodium sulfate), and the solvent is removed in vacuo. The residue is chromatographed (silica 9el, 25% ethyl acetate/75% hexane) to give the title compound as a yellow solid; mp 36.5°-37.5° C.

後処理

  1. customThe solvent is removed under reduced pressure
  2. customthe residue is partitioned between 200 mL of dichloromethane and 200 mL of water
  3. extractionThe aqueous layer is extracted with 100 mL of dichloromethane
  4. dry with materialthe combined organic layers are dried (sodium sulfate)
  5. customthe solvent is removed in vacuo
  6. customThe residue is chromatographed (silica 9el, 25% ethyl acetate/75% hexane)

出典と根拠

ORDレコード
ord-e103df3082474251a0fdaf2f6d2182ad
出典データセット
uspto-grants-1995_11
特許番号
US05466698

反応ノート

読み込み中…