Bromoacetonitrile → 7-Cyano-5-oxoheptanoic acid

HRID 465612

反応式

HRID 465612 の反応式
C[Si](C)(C)[N-][Si](C)(C)C.[K+].[O:11]=[C:12]([CH3:19])[CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17].Br[CH2:21][C:22]#[N:23]>O1CCCC1>[C:22]([CH2:21][CH2:19][C:12](=[O:11])[CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])#[N:23]

参加物

5

反応物 3

HCID 11534BromoacetonitrileHCID 184074-Acetylbutyric acidHCID 3251421Potassium bis(trimethylsilyl)amide

生成物 1

HCID 149867127-Cyano-5-oxoheptanoic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of potassium hexamethyldisilazide (66 ml, 60 mmol) in dry tetrahydrofuran (140 ml) at -70° is added slowly 5-oxohexanoic acid (36 ml, 30 mmol). The resulting yellow suspension is stirred at -70° for 1 h and bromoacetonitrile (2.2 ml, 32 mmol) is added slowly. The reaction mixture is stirred at -70° for 1 h and then at room temperature for 0.5 h. The reaction is quenched by addition of 1N aqueous hydrochloric acid (100 ml). The aqueous layer is extracted twice with ether. Combined organic layer is dried, filtered and evaporated to obtain a dark oil which is purified by silica gel chromatography using 9:1 ether/hexane with 1% acetic acid as eluent to give 7-cyano-5-oxoheptanoic acid as an oil.

後処理

  1. stirringThe reaction mixture is stirred at -70° for 1 h
  2. waitat room temperature for 0.5 h
  3. customThe reaction is quenched by addition of 1N aqueous hydrochloric acid (100 ml)
  4. extractionThe aqueous layer is extracted twice with ether
  5. customCombined organic layer is dried
  6. filtrationfiltered
  7. customevaporated
  8. customto obtain a dark oil which
  9. customis purified by silica gel chromatography

出典と根拠

ORDレコード
ord-8b89643d0bdd44568e4cd81cca446028
出典データセット
uspto-grants-1992_10
特許番号
US05153214

関連ノート

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