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

HRID 538883

反応式

HRID 538883 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-fecdf382f0564c6ebddbfea5285b64fe
出典データセット
uspto-grants-2014_10
特許番号
US08865752B2

関連ノート

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