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

HRID 1274870Notes

Reaction equation

HRID 1274870 reaction equation
[H-].[Na+].[O:3]=[C:4]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:8]([CH3:16])[O:7][CH2:6][N:5]1[C:17]([CH3:27])([CH3:26])[C:18]([CH:20]1[CH2:24][CH2:23][CH2:22][C:21]1=[CH2:25])=[O:19].IC.[C:30](OCC)(=O)C>O>[CH2:16]([C:8]1[O:7][CH2:6][N:5]([C:17]([CH3:27])([CH3:26])[C:18]([CH:20]2[CH2:24][CH2:23][CH2:22][C:21]2=[CH2:25])=[O:19])[C:4](=[O:3])[C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:30]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 221183222-(2,3-dihydro-4-oxo-6-methyl-5-phenyl-4H-1,3-oxazin-3-yl)-2-methyl-1-(2-methylenecyclopentyl)propan-1-one

Product 1

HCID 221183012-(2,3-dihydro-6-ethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methyl-1-(2-methylenecyclopentyl)propan-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (60%, 0.06 g) was added to a stirred solution of 2-(2,3-dihydro-4-oxo-6-methyl-5-phenyl-4H-1,3-oxazin-3-yl)-2-methyl-1-(2-methylenecyclopentyl)propan-1-one (0.45 g) at 20° C. After 10 minutes, iodomethane (0.1 ml) was added and stirring continued for 3 hours. Ethyl acetate and water were added and the organic phase dried (magnesium sulphate), evaporated and purified by silica gel column chromatography eluting with n-hexane/ethyl acetate (3:1) to give 2-(2,3-dihydro-6-ethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methyl-1-(2-methylenecyclopentyl)propan-1-one (Compound 1075, 0.15 g), NMR: 1.09(t,3H), 1.49(s,3H), 1.55(s,3H), 1.80-2.00(3H), 2.21(q,2H), 2.25-2.50(3H), 3.89(1H), 4.86(s,1H), 4.98(s,1H), 5.26(d,1H), 5.32(d,1H), 7.20-7.38(5H).

Workup

  1. waitcontinued for 3 hours
  2. dry with materialthe organic phase dried (magnesium sulphate)
  3. customevaporated
  4. custompurified by silica gel column chromatography
  5. washeluting with n-hexane/ethyl acetate (3:1)

Sources & evidence

ORD record
ord-b857ad4e88364e0892d025351d411a0d
Source dataset
uspto-grants-2000_12
Patent number
US06159902

Reaction notes

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