Dichloromethane → HCID 73680114, compound

HRID 1074560Notes

Reaction equation

HRID 1074560 reaction equation
C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:8][CH:9]=[O:10])C=CC=CC=1.ClC1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH:30]1[C:35]([C:36]([O:38][CH3:39])=[O:37])=[C:34]([CH:40]=O)[NH:33][C:32]([CH3:42])=[C:31]1[C:43]([OH:45])=[O:44].[CH2:46]([Cl:48])Cl>>[Cl:48][C:46]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH:30]1[C:35]([C:36]([O:38][CH3:39])=[O:37])=[C:34]([CH:40]=[CH:8][CH:9]=[O:10])[NH:33][C:32]([CH3:42])=[C:31]1[C:43]([OH:45])=[O:44]

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 20277354HCID 20277354, compound

Product 1

HCID 73680114HCID 73680114, compound

Procedure

To a solution of 2-triphenylphosphoranylideneacetaldehyde (1.9 g) in methylene chloride (15 ml) was added dropwise little by little a solution of isopropyl ester of 4-(2-chlorophenyl)-6-formyl-5-methoxycarbonyl-2-methyl-1,4-dihydropyridine-3-carboxylic acid (2.14 g) in methylene chloride (25 ml) with stirring over a period of 50 minutes, and the stirring was continued at ambient temperature for an hour. After removal of the methylene chloride from the reaction mixture, the residue was dissolved in benzene (10 ml) and subjected to column chromatography over silica gel (120 g). Elution was carried out with a mixture of benzene and ethyl acetate (10:1 by volume), and fractions containing a desired compound were collected and evaporated to dryness under reduced pressure to give orange needles of isopropyl ester of 4-(2-chlorophenyl)-6-(2-formylvinyl)-5-methoxycarbonyl-2-methyl-1,4-dihydropyridine-3-carboxylic acid (1.0 g), mp 179°-180.5° C.

Workup

  1. waitthe stirring was continued at ambient temperature for an hour
  2. customAfter removal of the methylene chloride from the reaction mixture
  3. dissolutionthe residue was dissolved in benzene (10 ml)
  4. washElution
  5. additionwas carried out with a mixture of benzene and ethyl acetate (10:1 by volume), and fractions
  6. additioncontaining a desired compound
  7. customwere collected
  8. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-1419faefae194f2ca3b4be6becca7436
Source dataset
uspto-grants-1983_07
Patent number
US04393070

Reaction notes

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