Hydrochloric Acid → 2-Ethoxyethyl 2-methyl-4-(3-nitrophenyl)-5-ethoxycarbonyl-6-hydroxymethyl-1,4-dihydropyridine-3-carboxylate

HRID 1248704ノート

反応式

HRID 1248704 の反応式
[CH3:1][C:2]1[NH:3][C:4]([CH:30]=[O:31])=[C:5]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:6]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)[C:7]=1[C:8]([O:10][CH2:11][CH2:12][O:13][CH2:14][CH3:15])=[O:9].[BH4-].[Na+].Cl>C(O)C>[CH3:1][C:2]1[NH:3][C:4]([CH2:30][OH:31])=[C:5]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:6]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)[C:7]=1[C:8]([O:10][CH2:11][CH2:12][O:13][CH2:14][CH3:15])=[O:9]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 133883552-Ethoxyethyl 2-methyl-4-(3-nitrophenyl)-5-ethoxycarbonyl-6-formyl-1,4-dihydropyridine-3-carboxylate

生成物 1

HCID 130921522-Ethoxyethyl 2-methyl-4-(3-nitrophenyl)-5-ethoxycarbonyl-6-hydroxymethyl-1,4-dihydropyridine-3-carboxylate収率 79.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a suspension of 2-ethoxyethyl 2-methyl-4-(3-nitrophenyl)-5-ethoxycarbonyl-6-formyl-1,4-dihydropyridine-3-carboxylate (1.13 g) in ethanol (15 ml) was added sodium borohydride (80 mg) with stirring under ice-cooling, and this mixture was further stirred for an hour at the same temperature. The reaction mixture was adjusted with dilute hydrochloric acid to pH 6 under ice-cooling and then the solvent was distilled off. To the residue was added water and the aqueous mixture was extracted with diethyl ether. The extract was washed with water and dried over magnesium sulfate. Removal of the solvent gave an oil, which was crystallized by treating with n-hexane. These were recrystallized from a mixture of diethyl ether and n-hexane to give pure crystals (900 mg) of 2-ethoxyethyl 2-methyl-4-(3-nitrophenyl)-5-ethoxycarbonyl-6-hydroxymethyl-1,4-dihydropyridine-3-carboxylate, m.p. 99° to 100° C.

後処理

  1. temperaturecooling
  2. stirringthis mixture was further stirred for an hour at the same temperature
  3. temperaturecooling
  4. distillationthe solvent was distilled off
  5. additionTo the residue was added water
  6. extractionthe aqueous mixture was extracted with diethyl ether
  7. washThe extract was washed with water
  8. dry with materialdried over magnesium sulfate
  9. customRemoval of the solvent
  10. customgave an oil, which
  11. customwas crystallized
  12. additionby treating with n-hexane
  13. customThese were recrystallized from a mixture of diethyl ether and n-hexane

出典と根拠

ORDレコード
ord-7fc88e8bd9684e66b46e91fb04287d9b
出典データセット
uspto-grants-1985_06
特許番号
US04525478

反応ノート

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