Pyridinium hydrochloride → 4-{5-Chloro-2-[(trimethylsilyl)ethynyl]phenyl}pyridin-2(1H)-one

HRID 56638

反応式

HRID 56638 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:16]#[C:17][Si:18]([CH3:21])([CH3:20])[CH3:19])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([O:14]C)[CH:9]=2)[CH:7]=1.Cl.[NH+]1C=CC=CC=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:16]#[C:17][Si:18]([CH3:19])([CH3:21])[CH3:20])=[C:6]([C:8]2[CH:13]=[CH:12][NH:11][C:10](=[O:14])[CH:9]=2)[CH:7]=1

参加物

3

反応物 2

HCID 21584435Pyridinium hydrochlorideHCID 1233889294-{5-Chloro-2-[(trimethylsilyl)ethynyl]phenyl}-2-methoxypyridine

生成物 1

HCID 1238372604-{5-Chloro-2-[(trimethylsilyl)ethynyl]phenyl}pyridin-2(1H)-one

実験手順

550 mg (purity 41%, 0.71 mmol) of 4-{5-chloro-2-[(trimethylsilyl)ethynyl]phenyl}-2-methoxypyridine and 20 eq. of pyridinium hydrochloride were reacted according to General Method 3A. The reaction mixture was concentrated under reduced pressure and water was added to the residue. After addition of ethyl acetate and phase separation, the organic phase was washed once with water, dried (sodium sulphate), filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (silica gel 60, cyclohexane/ethyl acetate and dichloromethane/methanol mixtures). Yield: 141 mg (purity 91%, 59% of theory)

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure and water
  2. additionwas added to the residue
  3. additionAfter addition of ethyl acetate and phase separation
  4. washthe organic phase was washed once with water
  5. dry with materialdried (sodium sulphate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by flash chromatography (silica gel 60, cyclohexane/ethyl acetate and dichloromethane/methanol mixtures)

出典と根拠

ORDレコード
ord-170c206dd1f84412a7fb90f74ab54455
出典データセット
uspto-grants-2016_09
特許番号
US09434690B2

関連ノート

読み込み中…