2,2,6-Trimethyl-5-phenyl-2H,4H-1,3-dioxin-4-one → Benzyl 2-methyl-2-(6-methyl-5-phenyl-2,3-dihydro-4-oxo-4H-1,3-oxazin-3-yl)-propionate

HRID 1600531Notes

Reaction equation

HRID 1600531 reaction equation
C[C:2]1(C)O[C:6](=[O:8])[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:4]([CH3:15])[O:3]1.C=[N:18][C:19]([CH3:31])([CH3:30])[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]>C1(C)C(C)=CC=CC=1>[CH3:31][C:19]([N:18]1[C:6](=[O:8])[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:4]([CH3:15])[O:3][CH2:2]1)([CH3:30])[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]

Participants

4

Reactant 2

HCID 131570242,2,6-Trimethyl-5-phenyl-2H,4H-1,3-dioxin-4-oneHCID 19354575benzyl 2-(N-methyleneamino)-2-methylpropanoate

Product 1

HCID 21829890Benzyl 2-methyl-2-(6-methyl-5-phenyl-2,3-dihydro-4-oxo-4H-1,3-oxazin-3-yl)-propionateYield 90.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To a mixture of 2,2,6-trimethyl-5-phenyl-4H-1,3-dioxin-4-one (13.97 g) and benzyl 2-(N-methylenamino)-2-methylpropionate (13.8 g) was added 130 ml of xylene, and the mixture was refluxed for 2 h. The solvent was evaporated and the residue was purified by chromatography on a silica gel column to get the captioned compound (21.1 g).

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. customThe solvent was evaporated
  3. customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-2dddb912c7ab46a78922a53c5fa25b94
Source dataset
uspto-grants-1999_11
Patent number
US05977025

Reaction notes

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