Diethyl Ether → HCID 22118288, compound

HRID 1274874Notes

Reaction equation

HRID 1274874 reaction equation
[CH3:1][C:2]1[O:7][CH2:6][N:5]([C:8]([CH3:18])([CH3:17])[C:9](=[O:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:4](=[O:19])[C:3]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[I:26][CH2:27][CH2:28][CH2:29][CH2:30]I.C(=O)([O-])[O-].[K+].[K+].CCOCC>CS(C)=O>[CH3:1][C:2]1[O:7][CH2:6][N:5]([C:8]([CH3:17])([CH3:18])[C:9](=[O:16])[CH:10]([CH2:30][CH2:29][CH2:28][CH2:27][I:26])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:4](=[O:19])[C:3]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 123371,4-DiiodobutaneHCID 22118254Ethyl 4-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-1,3-oxazin-3-yl)-4-methyl-3-oxo-pentanoate

Product 1

HCID 22118288HCID 22118288, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of ethyl 4-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-4-methyl-3-oxo-pentanoate (0.5 g), 1,4-diiodobutane(0.23 ml) and potassium carbonate(1.0 g) was stirred in dimethylsulphoxide at 20° C. for 12 hours. The mixture was diluted (ether), washed (brine), dried (MgSO4), evaporated and the residue purified by column chromatography (ethyl acetate/hexane 1:3) to give ethyl 4-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-(4'-iodobutyl)-4-methyl-3-oxo-pentanoate (0.3 g), NMR 1.24(3H, t), 1.3-1.4(2H, m), 1.43((3H, s), 1.48(3H, s), 1.7-2.0(7H, m), 3.12(2H, t), 3.8-3.9(1H, m), 4.1-4.2(2H, m), 5.28(2H, d), 7.2-7.4(5H, m).

Workup

  1. washwashed (brine)
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customthe residue purified by column chromatography (ethyl acetate/hexane 1:3)

Sources & evidence

ORD record
ord-646e96fad81743c1afb3b5b86544c806
Source dataset
uspto-grants-2000_12
Patent number
US06159902

Reaction notes

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