Diethyl Ether → 2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2,4-dimethylpentan-3-one

HRID 1003151Notes

Reaction equation

HRID 1003151 reaction equation
[CH3:1][C:2]1[O:7][CH2:6][N:5]([C:8]([CH3:15])([CH:10]([OH:14])[CH:11]([CH3:13])[CH3:12])[CH3:9])[C:4](=[O:16])[C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.CCOCC>ClCCl>[CH3:1][C:2]1[O:7][CH2:6][N:5]([C:8]([CH3:9])([C:10](=[O:14])[CH:11]([CH3:13])[CH3:12])[CH3:15])[C:4](=[O:16])[C:3]=1[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 187955302-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2,4-dimethylpentan-3-olHCID 178418287HCID 178418287, compound

Product 1

HCID 187954782-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2,4-dimethylpentan-3-oneYield 49.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2,4-dimethylpentan-3-ol (1.7 g) in dichloromethane was added to a stirred mixture of pyridinium chlorochromate (1.81 g) and powdered molecular sieve (4A) in dichloromethane at 20° C. After 5 hours, ether was added, the mixture filtered through hyflo and evaporated. The residue was purified by dry column chromatography on silica gel, eluting with dichloromethane/ethyl acetate to give 2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2,4-dimethylpentan-3-one (Compound 1, 0.84 g) as a white solid, m-p. 98.6-101.6° C.

Workup

  1. filtrationthe mixture filtered through hyflo
  2. customevaporated
  3. customThe residue was purified
  4. customby dry column chromatography on silica gel
  5. washeluting with dichloromethane/ethyl acetate

Sources & evidence

ORD record
ord-1d0ce245f19c45618819c65e0fc4c1ca
Source dataset
uspto-grants-2000_04
Patent number
US06046135

Reaction notes

Loading…