m-Chloroperbenzoic acid → 3-(4'-Bromo-biphenyl-4-yloxymethyl)-2-methoxy-pyridine 1-oxide

HRID 1716289ノート

反応式

HRID 1716289 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]3[C:17]([O:22][CH3:23])=[N:18][CH:19]=[CH:20][CH:21]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:32])C=1>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([O:14][CH2:15][C:16]3[C:17]([O:22][CH3:23])=[N+:18]([O-:32])[CH:19]=[CH:20][CH:21]=3)=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 685127243-(4'-Bromo-biphenyl-4-yloxymethyl)-2-methoxy-pyridine

生成物 1

HCID 685129393-(4'-Bromo-biphenyl-4-yloxymethyl)-2-methoxy-pyridine 1-oxide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A mixture of 3-(4′-bromo-biphenyl-4-yloxymethyl)-2-methoxy-pyridine (0.19 g, 0.51 mmol) from Step B and mCPBA (77% max., 0.25 g, 1.13 mmol) in dichloromethane (5 mL) was stirred at room temperature for 3 days. The reaction was diluted with dichloromethane and washed with aqueous Na2SO3 solution, 1N NaOH solution, water and brine. The organic layer was dried over anhydrous K2CO3 and filtered through Celite. The filtrate was concentrated under vacuo and the residue was purified by chromatography (silica gel, 10% MeOH/EtOAc) to give the desired product. MS: 386, 388 (M+H)+.

後処理

  1. washwashed with aqueous Na2SO3 solution, 1N NaOH solution, water and brine
  2. dry with materialThe organic layer was dried over anhydrous K2CO3
  3. filtrationfiltered through Celite
  4. concentrationThe filtrate was concentrated under vacuo
  5. customthe residue was purified by chromatography (silica gel, 10% MeOH/EtOAc)

出典と根拠

ORDレコード
ord-35d524410574471fafc78517b49a0945
出典データセット
uspto-grants-2010_09
特許番号
US07803793B2

反応ノート

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