2,2,2-Trifluoroethanol → 6-Methyl-4-(2,2,2-trifluoroethoxy)pyridine-2-carbonitrile

HRID 1880739ノート

反応式

HRID 1880739 の反応式
[H-].[Na+].[F:3][C:4]([F:8])([F:7])[CH2:5][OH:6].Cl[C:10]1[CH:15]=[C:14]([CH3:16])[N:13]=[C:12]([C:17]#[N:18])[CH:11]=1.[Cl-].[NH4+]>CN(C)C=O>[CH3:16][C:14]1[N:13]=[C:12]([C:17]#[N:18])[CH:11]=[C:10]([O:6][CH2:5][C:4]([F:8])([F:7])[F:3])[CH:15]=1

参加物

6

反応物 4

HCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 185052494-Chloro-6-methylpyridine-2-carbonitrile

生成物 1

HCID 595703876-Methyl-4-(2,2,2-trifluoroethoxy)pyridine-2-carbonitrile収率 92.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Into 8 ml of N,N-dimethylformamide was suspended 0.22 g of sodium hydride (60% oily), and 0.47 g of trifluoroethyl alcohol was added at 10° C. After stirring for 10 minutes, 0.6 g of 4-chloro-6-methylpyridine-2-carbonitrile was added at 0° C., the mixture was stirred for 1 hour, and the reaction solution was poured into an aqueous saturated ammonium chloride solution, followed by extraction with tert-butyl=methyl=ether three times. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.79 g of 6-methyl-4-(2,2,2-trifluoroethoxy)pyridine-2-carbonitrile.

後処理

  1. additionwas added at 10° C
  2. stirringthe mixture was stirred for 1 hour
  3. extractionfollowed by extraction with tert-butyl=methyl=ether three times
  4. washwashed with an aqueous saturated sodium chloride solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-80498211824f4b7bb03a2ec75f563384
出典データセット
uspto-grants-2012_11
特許番号
US08318776B2

反応ノート

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