Ethyl Acrylate → Ethyl 4-Cyano-5-methyl-4-(2-thienyl)hexanoate

HRID 1582770ノート

反応式

HRID 1582770 の反応式
[CH3:1][CH:2]([CH3:11])[CH:3]([C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)[C:4]#[N:5].[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[CH:13]=[CH2:14].CC(C)([O-])C.[K+].[Cl-].[NH4+]>O1CCCC1.[Cl-].[Na+].O.C(OCC)(=O)C.CCCCCC>[C:4]([C:3]([C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)([CH:2]([CH3:11])[CH3:1])[CH2:14][CH2:13][C:12]([O:16][CH2:17][CH3:18])=[O:15])#[N:5]

参加物

8

反応物 4

HCID 8821Ethyl AcrylateHCID 25517Ammonium ChlorideHCID 123819863-Methyl-2-(2-thienyl)butanenitrileHCID 23665647Potassium tert-butoxide

生成物 1

HCID 22718311Ethyl 4-Cyano-5-methyl-4-(2-thienyl)hexanoate収率 62.5%

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 21226206Ethyl acetate hexane溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

3-Methyl-2-(2-thienyl)butane nitrile 5.56 g 33.6 mmol and ethyl acrylate 4.00 ml 37.0 mmol were dissolved in tetrahydrofuran 100 ml. Potassium t-butoxide, 566 mg 5.04 mmol, was added little by little thereto at room temperature. Generation of heat continued during this step. After stirring for 1 hour, brine 100 ml and aqueous saturated ammonium chloride 150 ml were added thereto successively, and the mixture was extracted with ether 1 L. The organic layer was washed with brine 500 ml and water 500 ml successively, dried over magnesium sulfate anhydride and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane system), whereby the title compound (5.57 g 21.0 mmol, 62.5%) was obtained as a yellow oil.

後処理

  1. temperatureGeneration of heat
  2. extractionsuccessively, and the mixture was extracted with ether 1 L
  3. washThe organic layer was washed with brine 500 ml and water 500 ml successively
  4. dry with materialdried over magnesium sulfate anhydride
  5. customevaporated

出典と根拠

ORDレコード
ord-159b52f2ae32472d8d838766c1bbfc70
出典データセット
uspto-grants-2004_05
特許番号
US06737425B1

反応ノート

読み込み中…