Sodium Cyanide → Methyl 5-cyano-1-naphthoate

HRID 1166792

反応式

HRID 1166792 の反応式
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]([O:14][CH3:15])=[O:13].[C:16]([Cu])#[N:17].[C-]#N.[Na+]>CN(C=O)C.O>[C:16]([C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]([O:14][CH3:15])=[O:13])#[N:17]

参加物

6

反応物 3

HCID 8929Sodium CyanideHCID 4557673Methyl 5-bromo-1-naphthoateHCID 178418546HCID 178418546、化合物

生成物 1

HCID 826304Methyl 5-cyano-1-naphthoate収率 95%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of methyl 5-bromo-1-naphthylcarboxylate (5.2 g, 19 mmol) and CuCN (3.4 g, 38 mmol) in 100 mL anhydrous DMF was refluxed overnight. After cooling the reaction to 70° C., a solution of NaCN (2 g) in 50 mL water was added to destroy the copper complex. Ethyl acetate was added and the two layers were separated. The organic layer was washed with brine, dried over MgSO4, and concentrated. Silica gel column chromatography using hexane/ethyl acetate (5/1) gave the product (3.8 g, 95%).

後処理

  1. temperaturewas refluxed overnight
  2. temperatureAfter cooling
  3. customthe reaction to 70° C.
  4. customto destroy the copper complex
  5. additionEthyl acetate was added
  6. customthe two layers were separated
  7. washThe organic layer was washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-a4dd66e2a6f84475920f8b12515c57d9
出典データセット
uspto-grants-2003_09
特許番号
US06613942B1

関連ノート

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