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

HRID 1274868Notes

Reaction equation

HRID 1274868 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH3:12][C:13]1[O:18][CH2:17][N:16]([C:19]([CH3:29])([CH3:28])[CH:20]([CH:22]2[CH2:26][CH2:25][CH2:24][C:23]2=[CH2:27])[OH:21])[C:15](=[O:30])[C:14]=1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.CCOCC>ClCCl>[CH3:12][C:13]1[O:18][CH2:17][N:16]([C:19]([CH3:28])([CH3:29])[C:20]([CH:22]2[CH2:26][CH2:25][CH2:24][C:23]2=[CH2:27])=[O:21])[C:15](=[O:30])[C:14]=1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 221182782-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methyl-1-(2-methylenecyclopentyl)propan-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 221183222-(2,3-dihydro-4-oxo-6-methyl-5-phenyl-4H-1,3-oxazin-3-yl)-2-methyl-1-(2-methylenecyclopentyl)propan-1-oneYield 50.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Powdered molecular sieve (4 A, 17 g) and pyridinium chlorochromate (4.3 g) were added to a stirred solution of 2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methyl-1-(2-methylenecyclopentyl)propan-1-ol (3.1 g) in dichloromethane at 20° C. After 3 hours, ether was added and the mixture filtered, evaporated and the residue purified by silica gel column chromatography eluting with n-hexane/ethyl acetate (3:1) to give 2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methyl-1-(2-methylenecyclopentyl)propan-1-one (Compound 1072, 1.55 g), NMR: 1.49(s,3H), 1.55(s,3H), 1.93(s,3H), 1.85-2.00(3H) 2.25-2.52(2H), 3.89(1H), 4.87(s,1H), 5.28(2H), 7.2-7.4(5H).

Workup

  1. filtrationthe mixture filtered
  2. customevaporated
  3. customthe residue purified by silica gel column chromatography
  4. washeluting with n-hexane/ethyl acetate (3:1)

Sources & evidence

ORD record
ord-ae46e4449c6644bdb6e2ee1bc8e28f2f
Source dataset
uspto-grants-2000_12
Patent number
US06159902

Reaction notes

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