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

HRID 614611ノート

反応式

HRID 614611 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-38407f737f9f45e99a1efab0342745b2
出典データセット
uspto-grants-1979_03
特許番号
US04145432

反応ノート

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