Ethylene Glycol → 2-Bromo-5-(2-methyl-1,3-dioxolan-2-yl)pyridine

HRID 707235

反応式

HRID 707235 の反応式
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([Br:10])=[N:8][CH:9]=1)(=[O:3])[CH3:2].[CH2:11](O)[CH2:12][OH:13].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:10][C:7]1[CH:6]=[CH:5][C:4]([C:1]2([CH3:2])[O:13][CH2:12][CH2:11][O:3]2)=[CH:9][N:8]=1

参加物

5

反応物 3

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 156681955-Acetyl-2-bromopyridine

生成物 1

HCID 857750992-Bromo-5-(2-methyl-1,3-dioxolan-2-yl)pyridine収率 79%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
140 °C

実験手順

A mixture of 5-acetyl-2-bromopyridine (0.6 g, 3.00 mmol), ethylene glycol (0.535 ml, 9.60 mmol), p-toluenesulfonic acid monohydrate (0.171 g, 0.900 mmol), and toluene (12.00 ml) was stirred at 140° C. for 5 hours. The reaction mixture was washed with saturated sodium bicarbonate and brine. The aqueous layer was back extracted with ethyl acetate and the combined organics dried with magnesium sulfate and concentrated to give crude 2-bromo-5-(2-methyl-1,3-dioxolan-2-yl)pyridine (0.575 g, 2.356 mmol, 79% yield) as an orange oil. It was used without further purification.

後処理

  1. washThe reaction mixture was washed with saturated sodium bicarbonate and brine
  2. extractionThe aqueous layer was back extracted with ethyl acetate
  3. dry with materialthe combined organics dried with magnesium sulfate
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-709de68ecef14f7bb3f15a90f7ea0293
出典データセット
uspto-grants-2015_11
特許番号
US09174992B2

関連ノート

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