Diisopropylamine → 5-Hexenoic acid, 2-[(phenylmethylene)amino]-, methyl ester

HRID 260330

反応式

HRID 260330 の反応式
C(NC(C)C)(C)C.[CH2:8]([Li])[CH2:9][CH2:10][CH3:11].[CH3:13][O:14][C:15](=[O:25])[CH2:16][N:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.BrCCC=C.CN(C)P(N(C)C)(N(C)C)=O>O1CCCC1.CCCCCC.O>[CH3:13][O:14][C:15](=[O:25])[CH:16]([CH2:11][CH2:10][CH:9]=[CH2:8])[N:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

9

反応物 5

HCID 7912DiisopropylamineHCID 12679HexamethylphosphoramideHCID 21241Homoallyl bromideHCID 4169153Methyl [(phenylmethylidene)amino]acetateHCID 178418339Butyllithium

生成物 1

HCID 120394615-Hexenoic acid, 2-[(phenylmethylene)amino]-, methyl ester

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

Dissolve diisopropylamine (15.4 mL, 110 mmol) in tetrahydrofuran (250 mL), place under a nitrogen atmosphere and cool to -78° C. Add n-butyllithium (39 mL of a 2.7M solution in hexane, 105 mmol). Stir for 30 minutes and add, by dropwise addition, a solution of N-(phenylmethylene)glycine methyl ester (17.7 g, 100 mmol) in tetrahydrofuran (25 mL). Stir for 15 minutes and add 4-bromobutene (13.4 g, 100 mmol) and allow to warm slowly to room temperature. Add hexamethylphosphoramide (20 mL, 100 mmol) and stir under a nitrogen atmosphere for 3 hours. Pour into water, extract into ethyl ether and wash with brine several times. Dry (MgSO4) and evaporate the solvent in vacuo to give the title compound as an amber oil (25 g).

後処理

  1. additionadd, by dropwise addition
  2. stirringStir for 15 minutes
  3. temperatureto warm slowly to room temperature
  4. extractionextract into ethyl ether
  5. washwash with brine several times
  6. dry with materialDry (MgSO4)
  7. customevaporate the solvent in vacuo

出典と根拠

ORDレコード
ord-dee5893d9e76430ba5f39b6ebd3ce9ea
出典データセット
uspto-grants-1996_06
特許番号
US05527795

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