Phosphorus oxychloride → 4-(Benzyloxy)-2-chloropyridine

HRID 910888ノート

反応式

HRID 910888 の反応式
C(OC1C([Cl:15])=NC=CC=1)C1C=CC=CC=1.[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][NH:27][C:26](=O)[CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.P(Cl)(Cl)(Cl)=O>>[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][N:27]=[C:26]([Cl:15])[CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

4

反応物 3

HCID 24813Phosphorus oxychlorideHCID 8193743-(Benzyloxy)-2-chloropyridineHCID 36077244-Benzyloxy-2(1H)-pyridone

生成物 1

HCID 534041974-(Benzyloxy)-2-chloropyridine収率 47.1%

反応条件

温度
90 °C

実験手順

Preparation of 4-(benzyloxy-2-chloropyridine: A 250 mL round-bottomed flask was charged with 4-(benzyloxy)pyridin-2(1H)-one (10.0 g, 49.7 mmol) and phosphorus oxychloride (55.6 mL, 596 mmol). The reaction mixture was heated at 90° C. overnight, then cooled and carefully quenched with sodium carbonate and sodium hydroxide to pH 7. The aqueous layer was extracted with dichloromethane. The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography with dichloromethane as eluent to afford 4-(benzyloxy)-2-chloropyridine (5.14 g, 47.1% yield) as white solid. 1H NMR (CDCl3) δ 8.19 (d, 1H), 7.34-7.44 (m, 5H), 6.91 (d, 1H), 6.81 (dd, 1H), 5.10 (s, 2H). LC/MS: (5 to 95) Rt=2.64 min (ESI) m/z=220 (M+H) (40%).

後処理

  1. temperaturecooled
  2. customcarefully quenched with sodium carbonate and sodium hydroxide to pH 7
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography with dichloromethane as eluent

出典と根拠

ORDレコード
ord-aaaad3885f7546839a5ff59f82469729
出典データセット
uspto-grants-2011_09
特許番号
US08022222B2

反応ノート

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