Water → N-(1-Acetyl-1,2-dimethylpropyl)-4-chloro-α-methylbenzeneacetamide

HRID 992762Notes

Reaction equation

HRID 992762 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[O:11][C:12](=[O:19])[C:13]([CH:16]([CH3:18])[CH3:17])([CH3:15])[N:14]=2)[CH3:9])=[CH:4][CH:3]=1.C[Li].[CH3:22]COCC.C(OCC)(=O)C.O>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:9])[C:10]([NH:14][C:13]([CH3:15])([CH:16]([CH3:18])[CH3:17])[C:12](=[O:19])[CH3:22])=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 11312013HCID 11312013, compoundHCID 178467906HCID 178467906, compound

Product 1

HCID 11483313N-(1-Acetyl-1,2-dimethylpropyl)-4-chloro-α-methylbenzeneacetamideYield 55.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4.8 g (18 mmol) of 2-[1-(4-chlorophenyl)ethyl]-4-isopropyl-4-methyl-1,3-oxazol-5-one was dissolved in 40 ml of tetrahydrofuran. Thereto was dropwise added, at 5° C., a solution obtained by diluting 20.4 ml of a 1.14 M/liter methyllithium ether solution (23.3 mmol) with 50 ml of tetrahydrofuran. The mixture was kept at 10° C. or below and subjected to a reaction for 1 hour. After the completion of the reaction, ethyl acetate and water were added for phase separation. The separated organic layer was concentrated. The resulting concentrate was subjected to column chromatography to obtain 2.9 g (0.01 mol) (yield=55%) of 2-(4-chlorophenyl)-N-[1-methyl-1-isopropyl-2-oxopropyl]propanamide.

Workup

  1. additionThereto was dropwise added, at 5° C.
  2. customa solution obtained
  3. customwas kept at 10° C. or below
  4. customsubjected to a reaction for 1 hour
  5. additionwere added for phase separation
  6. concentrationThe separated organic layer was concentrated
  7. concentrationThe resulting concentrate

Sources & evidence

ORD record
ord-8f6e24c9241d4a908cb2d6ebe592f737
Source dataset
uspto-grants-2002_10
Patent number
US06469210B1

Reaction notes

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