Reaction #626065

Reaction equation

Iodoethane

N-(4-butyrylphenyl)acetamide

LDA THF

→

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

Solvents

THF

Conditions

Workup

1. 1
   workup.STIRRINGstirred overnight at RT
2. 2
   OtherThe reaction mixture was quenched with sat. aq. NH4Cl
3. 3
   Extractionextracted with ethyl acetate
4. 4
   DryingThe combined organic layers were dried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated
7. 7
   OtherThe crude product was purified by preparative TLC

Procedure

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+).

Source