6-Chloro-3-pyridinecarbonitrile → 6-(Octyloxy)pyridine-3-carbonitrile

HRID 128814

反応式

HRID 128814 の反応式
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][CH:3]=1.[CH2:10]([O-:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[Na+]>O>[CH2:10]([O:18][C:2]1[N:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][CH:3]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

参加物

4

反応物 2

HCID 51520946-Chloro-3-pyridinecarbonitrileHCID 23689331Sodium octylate

生成物 1

HCID 193751576-(Octyloxy)pyridine-3-carbonitrile収率 87.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 6-chloropyridine-3-carboxamide (14 g), phosphorous oxychloride (35 ml) and chloroform (120 ml) is refluxed for 2 hr, cooled, and concentrated. The residue is stirred with water and the resulting precipitate is collected and recrystallized from ethanol to provide 10.3 g (83 %) of 6-chloropyridine-3-carbonitrile. This nitrile (2.77 g) is added to a solution of sodium octanolate (prepared from 1-octanol (2.78 g) and sodium hydride (0.88g of 60% dispersion) in DMF (20 ml)). After 30 min at room temperature, the mixture is poured into water, and the product extracted with ether. The extracts are concentrated and chromatographed with 2:3 hexane-dichloromethane, to provide 6-(octyloxy)pyridine-3-carbonitrile as a colorless oil (3.7 g, 80%). This nitrile is dissolved in toluene (15 ml), cooled to -20°, and diisobutylaluminum hydride (12.5 ml of 1.5M solution in toluene) is added dropwise. After an hour, the mixture is poured into 1.0N hydrochloric acid and the product extracted with ether. The extracts are dried, filtered, and concentrated to leave 6-(octyloxy)pyridine-3-carboxaldehyde (2.36 g) as a yellow oil.

後処理

  1. extractionthe product extracted with ether
  2. concentrationThe extracts are concentrated
  3. customchromatographed with 2:3 hexane-dichloromethane

出典と根拠

ORDレコード
ord-25312700d82443b4a619336fff79f3f9
出典データセット
uspto-grants-1995_11
特許番号
US05464865

関連ノート

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