Water → 3-Methoxy-4-phenyl-4H-furo[3,2-b]indole-2-carboxylic acid

HRID 2164335ノート

反応式

HRID 2164335 の反応式
C[O:2][C:3]([C:5]1[O:16][C:15]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:7]=2[C:6]=1[O:23][CH3:24])=[O:4].[OH-].[Na+].O>CO>[CH3:24][O:23][C:6]1[C:7]2[N:8]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:15]=2[O:16][C:5]=1[C:3]([OH:4])=[O:2]

参加物

5

反応物 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 13220385HCID 13220385、化合物

生成物 1

HCID 132203943-Methoxy-4-phenyl-4H-furo[3,2-b]indole-2-carboxylic acid収率 45%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A suspension of 13.5 g (0.042 mole) of 3-methoxy-4-phenyl-4H-furo[3,2-b]indole-2-carboxylic acid methyl ester in 75 ml of methanol was treated with 70.6 ml of 1.0N aqueous sodium hydroxide. The mixture was stirred at reflux for 17 hours, then added to 1.4 l of water. The insoluble material was filtered, added to 1.0 l of water, and acidified with acetic acid while cooling in an ice bath. The crude acid product was recovered by filtration. The original filtrate from the reaction mixture and 1.4 l of water was also cooled in ice and acidified with acetic acid. The crude product obtained was filtered and combined with the earlier crop. The combined crude products were stirred in 400 ml of water, filtered, and recrystallized from methanol. There are obtained 5.8 g (45% yield) of analytically pure acid, mp 154°-155° C.

後処理

  1. temperatureat reflux for 17 hours
  2. filtrationThe insoluble material was filtered
  3. additionadded to 1.0 l of water
  4. temperaturewhile cooling in an ice bath
  5. filtrationThe crude acid product was recovered by filtration
  6. temperatureThe original filtrate from the reaction mixture and 1.4 l of water was also cooled in ice

出典と根拠

ORDレコード
ord-ff75efe93967467383a97ed42f11bd65
出典データセット
uspto-grants-1985_03
特許番号
US04503236

反応ノート

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