Benzyl Bromide → 2-(Benzyloxy)-4-methylpyridine

HRID 1486237노트

반응식

HRID 1486237 반응식
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][N:11]=1>C1COCC1.C(=O)([O-])[O-].[Ag+2]>[CH2:1]([O:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 7498Benzyl BromideHCID 178428601HCID 178428601, 화합물

생성물 1

HCID 142234762-(Benzyloxy)-4-methylpyridine수율 94.2%

시약·촉매·용매 2

HCID 178418647HCID 178418647, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 13.6 ml (114 mmol, 1.0 eq.) of benzyl bromide and 15.0 g (137 mmol, 1.2 eq.) of 2-hydroxy-4-methylpyridine [CAS No: 13466-41-6] was dissolved in 470 ml of THF. The solution was admixed with 37.9 g (137 mmol, 1.2 eq.) of silver carbonate and the mixture was heated to reflux with exclusion of light overnight. Subsequently, the reaction mixture was filtered through kieselguhr and eluted with ethyl acetate, and the filtrate was concentrated. The crude product was purified by silica gel chromatography (700 g of silica gel, cyclohexane/ethyl acetate 95:5). 21.4 g of the title compound were obtained (94% of theory).

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux with exclusion of light overnight
  3. filtrationSubsequently, the reaction mixture was filtered through kieselguhr
  4. washeluted with ethyl acetate
  5. concentrationthe filtrate was concentrated
  6. customThe crude product was purified by silica gel chromatography (700 g of silica gel, cyclohexane/ethyl acetate 95:5)

출처 및 근거

ORD 기록
ord-aa12926c7dfe431ebadb71396f925803
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422285B2

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