Hexane → Diethyl 2-methyl-4-(2-thienyl)-6-hydroxymethyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 1759080Notes

Reaction equation

HRID 1759080 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH:23]=[O:24])=[C:5]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:6]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[BH4-].[Na+].CCCCCC>C(O)C.C(OCC)(=O)C>[CH3:1][C:2]1[NH:3][C:4]([CH2:23][OH:24])=[C:5]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:6]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

6

Reactant 3

HCID 8058HexaneHCID 4311764Sodium borohydrideHCID 11245008Diethyl 2-methyl-4-(2-thienyl)-6-formyl-1,4-dihydropyridine-3,5-dicarboxylate

Product 1

HCID 13469472Diethyl 2-methyl-4-(2-thienyl)-6-hydroxymethyl-1,4-dihydropyridine-3,5-dicarboxylateYield 90.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of diethyl 2-methyl-4-(2-thienyl)-6-formyl-1,4-dihydropyridine-3,5-dicarboxylate (940.68 mg) in 99% ethanol (30 ml) was gradually added sodium borohydride (113.5 mg) under stirring and this was further stirred at room temperature for 2 hours. After removal of ethanol, the residue was extracted with ethyl acetate and the extract was washed twice with water and then dried. The solvent was removed from the extract to give a pale yellow oil. The oil was pulverized with n-hexane. The powder was dissolved in ethyl acetate. After collecting by filtration of the insoluble product, to the filtrate was added n-hexane and the mixture was allowed to stand in refrigerator. The appearring crystals were collected by filtration to give pale yellow granules (857.2 mg) of diethyl 2-methyl-4-(2-thienyl)-6-hydroxymethyl-1,4-dihydropyridine-3,5-dicarboxylate, m.p. 125° to 126° C.

Workup

  1. stirringthis was further stirred at room temperature for 2 hours
  2. customAfter removal of ethanol
  3. extractionthe residue was extracted with ethyl acetate
  4. washthe extract was washed twice with water
  5. customdried
  6. customThe solvent was removed from the
  7. extractionextract
  8. customto give a pale yellow oil
  9. filtrationAfter collecting by filtration of the insoluble product, to the filtrate
  10. additionwas added n-hexane
  11. filtrationThe appearring crystals were collected by filtration

Sources & evidence

ORD record
ord-1cf2eefbfcdd4f6d90b80a458f30b562
Source dataset
uspto-grants-1982_07
Patent number
US04338322

Reaction notes

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