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

HRID 1894767Notes

Reaction equation

HRID 1894767 reaction equation
[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.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]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 2724682Lithium diisopropylamideHCID 4304236N-(4-Butyrylphenyl)acetamide

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of N-(4-butyrylphenyl)acetamide (3 g, 14.6 mmol) in THF (300 mL) was added 2.0 M LDA in 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+).

Workup

  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

Sources & evidence

ORD record
ord-acc302f343d14b3a8b57885f9d9dcb49
Source dataset
uspto-grants-2013_08
Patent number
US08513291B2

Reaction notes

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