Diethyl Ether → HCID 22118326, compound

HRID 1274859Notes

Reaction equation

HRID 1274859 reaction equation
[H-].[Na+].[CH3:3][C:4]1[O:9][CH2:8][N:7]([C:10]([CH3:21])([CH3:20])[C:11](=[O:19])[CH:12]([CH3:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:6](=[O:22])[C:5]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH3:29]COCC>CN(C)C=O>[CH3:3][C:4]1[O:9][CH2:8][N:7]([C:10]([CH3:20])([CH3:21])[C:11](=[O:19])[C:12]([CH3:29])([CH3:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:6](=[O:22])[C:5]=1[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 22118311HCID 22118311, compound

Product 1

HCID 22118326HCID 22118326, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (67 mg of 60%) was added to a stirred solution of ethyl 4-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2,4-dimethyl-3-oxo-pentanoate (0.4 g) in N,N-dimethylformamide at 0° C. lodomethane (0.1 ml) was added and stirring continued for 16 hours. Ether was added and the organic phase washed (brine), dried (magnesium sulphate), evaporated and the residue purified by column chromatography eluting with ethyl acetate/hexane (1:2) to give ethyl 4-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2,2,4-trimethyl-3-oxo-pentanoate (Compound 197, 0.3 g), NMR 1.21(3H, t), 1.47(6H, s), 1.52(6H, s), 1.92(3H, s), 4.13(2H, q), 5.16(2H, s), 7.2-7.4(5H, m).

Workup

  1. additionwas added
  2. washthe organic phase washed (brine)
  3. dry with materialdried (magnesium sulphate)
  4. customevaporated
  5. customthe residue purified by column chromatography
  6. washeluting with ethyl acetate/hexane (1:2)

Sources & evidence

ORD record
ord-248b294f383340229e841956a512beba
Source dataset
uspto-grants-2000_12
Patent number
US06159902

Reaction notes

Loading…