Carbon Tetrachloride → HCID 19871297, compound

HRID 569592Notes

Reaction equation

HRID 569592 reaction equation
[Cl:1][C:2]1C(Cl)=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:19])[NH:12][C:11]([CH2:20][O:21][CH2:22][CH:23](O)[CH2:24][OH:25])=[C:10]1[C:27]([O:29][CH2:30][CH3:31])=[O:28].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:51]([Cl:55])(Cl)(Cl)Cl>O>[Cl:1][C:2]1[C:51]([Cl:55])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:19])[NH:12][C:11]([CH2:20][O:21][CH2:22][CH:23]2[CH2:24][O:25]2)=[C:10]1[C:27]([O:29][CH2:30][CH3:31])=[O:28]

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 14810588HCID 14810588, compound

Product 1

HCID 19871297HCID 19871297, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1- {[4-(2.3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl]methoxy}-2,3-dihydroxypropane (4.74 g) (see Example 20) and triphenylphosphine (2.62 g) in carbon tetrachloride (60 ml) was heated under reflux for 4 hours and then diluted with dichloroaethane and water. The layers were separated and the aqueous layer was extracted into dichloromethane. The combined organic layers were washed with water, dried over Na2SO4 and evaporated. The residue was purified by chromatography on SiO2 (80 g) using toluene plus 0-20% ethyl acetate as the eluant. Appropriate fractions were combined and evaporated and the residue triturated with diisopropyl ether. The resulting solid was collected, washed with diisopropyl ether and dried to give the title compound (1.40 g), m.p. 103°-104° C.

Workup

  1. temperatureunder reflux for 4 hours
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted into dichloromethane
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe residue was purified by chromatography on SiO2 (80 g)
  8. customevaporated
  9. customthe residue triturated with diisopropyl ether
  10. customThe resulting solid was collected
  11. washwashed with diisopropyl ether
  12. customdried

Sources & evidence

ORD record
ord-55ddfd56bb274bbf935c23442b700e94
Source dataset
uspto-grants-1988_03
Patent number
US04732985

Reaction notes

Loading…