Diisopropylamine → HCID 86749012, 화합물

HRID 375792

반응식

HRID 375792 반응식
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

참가 물질

7

반응물 4

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

생성물 1

HCID 86749012HCID 86749012, 화합물수율 46%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

반응 조건

온도
-78 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-b51fd227c4b1438ebcfe790c15ede657
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05488047

연결된 노트

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