Sodium borohydride → Ethyl 4-chloro-6-[4-(hydroxymethyl)phenoxy]-1-methyl-2-indolecarboxylate

HRID 565051ノート

反応式

HRID 565051 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]=[O:19])=[CH:14][CH:13]=2)[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:6]2[CH3:20].[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:10]=[C:9]([O:11][C:12]2[CH:13]=[CH:14][C:15]([CH2:18][OH:19])=[CH:16][CH:17]=2)[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:6]2[CH3:20]

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 21194191Ethyl 4-chloro-6-(4-formylphenoxy)-1-methyl-2-indolecarboxylate

生成物 1

HCID 21194045Ethyl 4-chloro-6-[4-(hydroxymethyl)phenoxy]-1-methyl-2-indolecarboxylate収率 100.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
0 °C

実験手順

A mixture of 0.90 g (2.52 mmol) of ethyl 4-chloro-6-[4-formylphenoxy)-1-methyl-2-indolecarboxylate, 0.10 g (2.52 mmol) of sodium borohydride and 20 ml of ethanol was stirred at 0° C. for 2 hours. The reaction mixture was poured onto ice water. The resulting mixture was then extracted three times with ethyl acetate. The combined extracts were washed with saturated sodium chloride aqueous solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to give 0.91 g (>99%) of ethyl 4-chloro-6-[4-(hydroxymethyl)phenoxy]-1-methyl-2-indolecarboxylate.

後処理

  1. additionThe reaction mixture was poured onto ice water
  2. extractionThe resulting mixture was then extracted three times with ethyl acetate
  3. washThe combined extracts were washed with saturated sodium chloride aqueous solution
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-cd5b24dc4c7f47cfa0c594d0a29841fb
出典データセット
uspto-grants-2001_01
特許番号
US06169107A

反応ノート

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