Diisopropylamine → HCID 86749012、化合物

HRID 375792

反応式

HRID 375792 の反応式
C(N[CH:5]([CH3:7])[CH3:6])(C)C.[CH2:8]([Li])CCC.[C:13]([O:23][CH2:24][CH3:25])(=[O:22])[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Br[CH2:27][C:28]([O:30]C(C)(C)C)=[O:29]>O1CCCC1.CCCCCC>[C:16]1([CH2:15][C:14]([CH2:27][C:28]([OH:30])=[O:29])([C:5]([CH3:6])([CH3:7])[CH3:8])[C:13]([O:23][CH2:24][CH3:25])=[O:22])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

参加物

7

反応物 4

HCID 7912DiisopropylamineHCID 16237Ethyl 3-phenylpropionateHCID 79177tert-Butyl bromoacetateHCID 178418339Butyllithium

生成物 1

HCID 86749012HCID 86749012、化合物収率 46%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

Dissolve diisopropylamine (3.5 mL, 25 mmol) in tetrahydrofuran (30 mL). Add n-butyllithium (14 mL of a 1.6 M solution in hexane, 22.4 mmol). Stir for 15 minutes and cool to -78° C. Add, by dropwise addition, ethyl dihydrocinnamate (3.5 mL, 20 mmol) and stir for 30 minutes. Add t-butyl bromoacetate (4.0 mL, 25 mmol) and gradually warm to room temperature overnight. Quench the solution with ammonium chloride solution (10 mL) and partition between water (25 mL) and ethyl ether (50 mL). Separate the organic phase, dry (MgSO4) and evaporate the solvent in vacuo. Purify by silica gel chromatography (5% ethyl acetate/hexane) to give 3-phenyl-2-t-butylcarboxymethylpropionic acid, ethyl ester as a pale yellow oil (2.68 g, 46%).

後処理

  1. stirringstir for 30 minutes
  2. customQuench the solution with ammonium chloride solution (10 mL)
  3. custompartition between water (25 mL) and ethyl ether (50 mL)
  4. customSeparate the organic phase
  5. dry with materialdry (MgSO4)
  6. customevaporate the solvent in vacuo
  7. customPurify by silica gel chromatography (5% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-b51fd227c4b1438ebcfe790c15ede657
出典データセット
uspto-grants-1996_01
特許番号
US05488047

関連ノート

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