Water → 6-Bromo-3-isopropoxy-2-methylpyridine

HRID 72922ノート

反応式

HRID 72922 の反応式
[Br:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([OH:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH:17]([CH3:19])[CH3:18].O>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([O:9][CH:17]([CH3:19])[CH3:18])=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 962WaterHCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 111947876-Bromo-2-methylpyridin-3-ol

生成物 1

HCID 866685246-Bromo-3-isopropoxy-2-methylpyridine収率 85%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

6-Bromo-2-methylpyridin-3-ol (10.5 g, 55.9 mmol) was dissolved in DMF (100 mL). K2CO3 (19.3 g, 139.6 mmol) and 2-bromopropane (13.1 ml, 139.6 mmol) were added to the solution and the reaction mixture was heated at 100° C. overnight. The reaction mixture was poured onto a mixture of water and EtOAc (200 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2×). The combined organic layers were dried (Na2SO4) and concentrated in vacuo. The crude oil was purified by silica gel column chromatography (0-20% ethyl acetate/heptanes) to give 6-bromo-3-isopropoxy-2-methylpyridine (10.9 g, 85%) as a yellow oil. 1H-NMR (300 MHz, CDCl3) 1.42 (d, 6H), 2.48 (s, 3H), 4.65 (m, 1H), 7.20 (d, 1H), 8.04 (d, 1H).

後処理

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc (2×)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude oil was purified by silica gel column chromatography (0-20% ethyl acetate/heptanes)

出典と根拠

ORDレコード
ord-4230d3130cd940e6a25e34a934d55773
出典データセット
uspto-grants-2014_09
特許番号
US08828996B2

反応ノート

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