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

HRID 910888노트

반응식

HRID 910888 반응식
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

참가 물질

4

반응물 3

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

생성물 1

HCID 534041974-(Benzyloxy)-2-chloropyridine수율 47.1%

반응 조건

온도
90 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-aaaad3885f7546839a5ff59f82469729
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022222B2

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