4-Methylbenzaldehyde → HCID 22456887, compound

HRID 2186563Notes

Reaction equation

HRID 2186563 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([CH:7]=[O:8])=[CH:3][CH:2]=1.[CH2:10]([NH2:14])[CH2:11][CH2:12][CH3:13].C1C[O:18][CH2:17]C1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(#N)C>[CH2:10]([NH:14][C:17](=[O:18])[CH:7]([OH:8])[C:4]1[CH:5]=[CH:6][C:1]([CH3:9])=[CH:2][CH:3]=1)[CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 77254-MethylbenzaldehydeHCID 8007ButylamineHCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 22456887HCID 22456887, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of p-tolualdehyde (131 mg, 1.0 mmol) and 1 (216 mg, 1.2 mmol) in acetonitrile (3 ml) was added n-butylamine (80 mg, 1.1 mmol) at 0° C. After stirring for 5 min, the reaction mixtures was added dropwise THF solution of tetrabutylammonium fluoride (1.0 N, 1.5 ml, 1.5 mmol), and then stirred at 0° C. for 20 min. The resulting reaction solution was concentrated and purified with silica gel column chromatography by using hexane-ethyl acetate (3/1) as an eluent to give N-butyl-2-hydroxy-2-(4-methylphenyl)acetamide as a colorless powder (218 mg, 0.94 mmol, 94%).

Workup

  1. customthe reaction mixtures
  2. stirringstirred at 0° C. for 20 min
  3. customThe resulting reaction solution
  4. concentrationwas concentrated
  5. custompurified with silica gel column chromatography

Sources & evidence

ORD record
ord-f6592c07912f411ca091f014f8fae07c
Source dataset
uspto-grants-2002_06
Patent number
US06403818B1

Reaction notes

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