Sodium hydride → 2-(5-Bromo-alpha-cyano-2-methoxymethoxybenzyl)-3-trifluoromethyl-pyridine

HRID 862079ノート

反応式

HRID 862079 の反応式
[H-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:13][CH2:14][O:15][CH3:16])=[C:8]([CH:12]=1)[CH2:9][C:10]#[N:11].Cl[C:18]1[C:23]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:21]=[CH:20][N:19]=1.C1(C)C=CC(S([O-])=O)=CC=1.[Na+]>CN(C=O)C>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:13][CH2:14][O:15][CH3:16])=[C:8]([CH:12]=1)[CH:9]([C:18]1[C:23]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:21]=[CH:20][N:19]=1)[C:10]#[N:11]

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 5898332-Chloro-3-(trifluoromethyl)pyridineHCID 2723791Sodium p-toluenesulfinateHCID 197016225-Bromo-2-methoxymethoxybenzyl cyanide

生成物 1

HCID 197016212-(5-Bromo-alpha-cyano-2-methoxymethoxybenzyl)-3-trifluoromethyl-pyridine収率 48%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Sixty % sodium hydride (656 mg) was added, at room temperature, to a mixture of 5-bromo-2-methoxymethoxybenzyl cyanide (3.50 g), 2-chloro-3-trifluoromethylpyridine (2.48 g), sodium p-toluenesulfinate (731 mg) and DMF (35 ml), followed by stirring for 30 minutes at the same temperature under argon atmosphere. The reaction mixture was poured into an aqueous saline solution, followed by extraction with ethyl acetate. The extract solution was washed with an aqueous saline solution, dried (anhydrous sodium sulfate) and concentrated. The concentrate was purified by means of a silica gel column chromatography (eluent: ethyl acetate/hexane) to give 2-(5-bromo-α-cyano-2-methoxymethoxybenzyl)-3-trifluoromethyl-pyridine (2.63 g) (Compound D-4). The physical properties and spectrum date are shown in Table 13 and Table 14.

後処理

  1. additionThe reaction mixture was poured into an aqueous saline solution
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe extract solution was washed with an aqueous saline solution
  4. dry with materialdried (anhydrous sodium sulfate)
  5. concentrationconcentrated
  6. customThe concentrate was purified by means of a silica gel column chromatography (eluent: ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-866fbdae74064f1b922de30c2f7a7604
出典データセット
uspto-grants-1998_02
特許番号
US05716971

反応ノート

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