HCID 22118265, compound → HCID 22118334, compound

HRID 1274863Notes

Reaction equation

HRID 1274863 reaction equation
[CH3:1][C:2]1[O:7][CH2:6][N:5]([C:8]([CH3:20])([CH3:19])[CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]=[CH2:18])[CH:12]=2)[OH:10])[C:4](=[O:21])[C:3]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[CH3:1][C:2]1[O:7][CH2:6][N:5]([C:8]([CH3:19])([CH3:20])[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]=[CH2:18])[CH:12]=2)=[O:10])[C:4](=[O:21])[C:3]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 22118265HCID 22118265, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 22118334HCID 22118334, compound

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-methyl-1-(3-vinylphenyl)propan-1-ol) (0.28 g) in dichloromethane was added to a stirred mixture of pyridinium chlorochromate (0.38 g) and powdered molecular sieve (4A) in dichloromethane at 20° C. After 3 hours the mixture was purified by dry column chromatography on silica gel, eluting with hexane, increasing the polarity to hexane/ethyl acetate (1:1), to give 2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methyl-1-(3-vinylphenyl)propan-1-one (Compound 444, 0.05 g) as a white solid, NMR 1.6 (s,6H), 1.8 (s,3H), 5.2 (d,1H), 5.3 (s,2H), 5.7 (d,1H), 6.6 (m,1H), 6.9 (m,2H), 7.2 (m,5H), 7.4 (d,1H), 7.8 (d,1H), 8.0 (s,1H).

Workup

  1. customAfter 3 hours the mixture was purified
  2. customby dry column chromatography on silica gel
  3. washeluting with hexane
  4. temperatureincreasing the polarity to hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-d5211ef6947f4564a48fc84949688617
Source dataset
uspto-grants-2000_12
Patent number
US06159902

Reaction notes

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