p-Toluenesulfonic acid → 2-Bromo-5-(dimethoxymethyl)pyridine

HRID 885836ノート

反応式

HRID 885836 の反応式
[Br:1][C:2]1[N:7]=[CH:6][C:5](C=O)=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:21](OC)([O:24][CH3:25])[O:22][CH3:23].C([O-])(O)=O.[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:21]([O:24][CH3:25])[O:22][CH3:23])=[CH:6][N:7]=1

参加物

6

反応物 4

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 516892Sodium BicarbonateHCID 117692346-Bromo-3-pyridinecarboxaldehyde

生成物 1

HCID 64252132-Bromo-5-(dimethoxymethyl)pyridine収率 95.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of 6-bromopyridine-3-carbaldehyde (3.07 g, 16.5 mmol), p-toluenesulfonic acid (386 mg, 2.02 mmol) and trimethyl orthoformate (1.97 ml, 18 mmol) in MeOH (80 ml) was stirred at room temperature for 48 hours. The mixture was then brought to basic conditions with a 5% NaHCO3 solution and extracted twice with diethyl ether. The pooled organic phases were dried over Na2SO4 and evaporated to dryness to give 3.66 g of 2-bromo-5-dimethoxymethyl-pyridine as a pale yellow oil.

後処理

  1. extractionextracted twice with diethyl ether
  2. dry with materialThe pooled organic phases were dried over Na2SO4
  3. customevaporated to dryness

出典と根拠

ORDレコード
ord-da5f42b359da4c28b399296303b378bb
出典データセット
uspto-grants-2012_08
特許番号
US08242175B2

反応ノート

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