Iodoethane → N-(4-(2-ethylbutanoyl)phenyl)acetamide

HRID 538883

반응식

HRID 538883 반응식
[C:1]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:15])[CH3:14])=[CH:8][CH:7]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].[Li+].[CH3:17][CH:18]([N-]C(C)C)C.C1COCC1.ICC>C1COCC1>[CH2:3]([CH:2]([CH2:17][CH3:18])[C:1]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:15])[CH3:14])=[CH:8][CH:7]=1)=[O:5])[CH3:4]

참가 물질

5

반응물 3

HCID 6340IodoethaneHCID 4304236N-(4-Butyrylphenyl)acetamideHCID 10997623Lithium diisopropylamide mono(tetrahydrofuran)

생성물 1

HCID 43160160N-(4-(2-ethylbutanoyl)phenyl)acetamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a solution of N-(4-butyrylphenyl)acetamide (3 g, 14.6 mmol) in THF (300 mL) was added 2.0 M LDA THF (18.3 mL) at −78° C. and then the reaction mixture was stirred for 1 h at −78° C. Iodoethane was added and stirred overnight at RT. The reaction mixture was quenched with sat. aq. NH4Cl and then extracted with ethyl acetate. The combined organic layers were dried over MgSO4, filtered and then concentrated. The crude product was purified by preparative TLC using 50% ethyl acetate in hexane as eluent to afford N-(4-(2-ethylbutanoyl)phenyl)acetamide as white solid. MS (ES+): m/z 234.28 (MH+).

후처리

  1. stirringstirred overnight at RT
  2. customThe reaction mixture was quenched with sat. aq. NH4Cl
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by preparative TLC

출처 및 근거

ORD 기록
ord-fecdf382f0564c6ebddbfea5285b64fe
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865752B2

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