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

HRID 614611노트

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HRID 614611 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

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 appearing 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.

후처리

  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 appearing crystals were collected by filtration

출처 및 근거

ORD 기록
ord-38407f737f9f45e99a1efab0342745b2
출처 데이터셋
uspto-grants-1979_03
특허 번호
US04145432

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