Water → Methyl 5-(benzyloxy)-6-chloronicotinate

HRID 709795ノート

反応式

HRID 709795 の反応式
[Cl:1][C:2]1[C:11]([OH:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[H-].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CN(C=O)C>[CH2:15]([O:12][C:11]1[C:2]([Cl:1])=[N:3][CH:4]=[C:5]([CH:10]=1)[C:6]([O:8][CH3:9])=[O:7])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

6

反応物 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 46941479Methyl 6-chloro-5-hydroxynicotinate

生成物 1

HCID 71496987Methyl 5-(benzyloxy)-6-chloronicotinate収率 38.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a solution of methyl 6-chloro-5-hydroxynicotinate (10.5 g) in DMF (80 mL) was added 60% sodium hydride (2.80 g) at 0° C., and the mixture was stirred at 0° C. for 0.5 hr. Benzyl bromide (10.5 g) was added, and the mixture was stirred at room temperature for 20 hr. The reaction mixture was poured into water, and the precipitate was collected by filtration. The crude crystals were purified by silica gel column chromatography (petroleum ether/THF) to give the title compound (6.00 g) as a white solid.

後処理

  1. stirringthe mixture was stirred at room temperature for 20 hr
  2. filtrationthe precipitate was collected by filtration
  3. customThe crude crystals were purified by silica gel column chromatography (petroleum ether/THF)

出典と根拠

ORDレコード
ord-dfd1e4923bb4438c84b11435905ef818
出典データセット
uspto-grants-2015_11
特許番号
US09181186B2

反応ノート

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