2,2,6-Trimethyl-4H-1,3-dioxin-4-one → N-(4-tert-butylbenzyl)-3-oxobutanamide

HRID 1961470Notes

Reaction equation

HRID 1961470 reaction equation
CC1(C)O[C:6](=[O:8])[CH:5]=[C:4]([CH3:9])[O:3]1.[C:11]([C:15]1[CH:20]=[CH:19][C:18]([CH2:21][NH2:22])=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12]>C1(C)C=CC=CC=1.CCOC(C)=O>[C:11]([C:15]1[CH:16]=[CH:17][C:18]([CH2:21][NH:22][C:6](=[O:8])[CH2:5][C:4](=[O:3])[CH3:9])=[CH:19][CH:20]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 2

HCID 793682,2,6-Trimethyl-4H-1,3-dioxin-4-oneHCID 27356554-tert-Butylbenzylamine

Product 1

HCID 86661979N-(4-tert-butylbenzyl)-3-oxobutanamideYield 56%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

2,2,6-Trimethyl-4H-1,3-dioxin-4-one (1.6 ml, 12.09 mmol) and (4-tert-butylphenyl)methanamine (2.0 ml, 11.36 mmol) were dissolved in toluene (2 ml) and heated at 130° C. for 28 hours. Reaction was cooled to room temperature and diluted with EtOAc (40 ml). The organic phase was washed with HCl (2*30 ml, 1M) and NaHCO3 (2*30 ml, sat aq), dried over MgSO4 and evaporated. The crude product was purified by precipitation from toluene/pet.ether to give 1.57 g (56%) of N-(4-tert-butylbenzyl)-3-oxobutanamide as a pale powder.

Workup

  1. customReaction
  2. temperaturewas cooled to room temperature
  3. washThe organic phase was washed with HCl (2*30 ml, 1M) and NaHCO3 (2*30 ml, sat aq)
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe crude product was purified by precipitation from toluene/pet

Sources & evidence

ORD record
ord-5b19018fbdb343ff9348146d0b3a4d77
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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