Dimethyl Sulfoxide → 3-(6-carboxyhex-1-enyl)-N-(3-pyridyl)indole

HRID 485346ノート

反応式

HRID 485346 の反応式
CS(C)=O.C([Li])CCC.[Br-].[C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:13])=[O:12].[N:38]1[CH:43]=[CH:42][CH:41]=[C:40]([N:44]2[C:52]3[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=3)[C:46]([CH:53]=O)=[CH:45]2)[CH:39]=1>O>[C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH:18]=[CH:53][C:46]1[C:47]2[C:52](=[CH:51][CH:50]=[CH:49][CH:48]=2)[N:44]([C:40]2[CH:39]=[N:38][CH:43]=[CH:42][CH:41]=2)[CH:45]=1)([OH:13])=[O:12]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 2779280(5-Carboxypentyl)triphenylphosphanium bromideHCID 13490349HCID 13490349、化合物HCID 178418339Butyllithium

生成物 1

HCID 541584553-(6-carboxyhex-1-enyl)-N-(3-pyridyl)indole

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of dimsyllithium (from 80 ml of dimethylsulfoxide and 13 ml of 2.1M n-butyllithium) is stirred under nitrogen at room temperature, and 6.2 g of 5-carboxypentyltriphenylphosphonium bromide is added in portions. The reaction mixture is stirred for 30 minutes and 3.0 g of N-(3-pyridyl)indole-3-carboxaldehyde is added. After 18 hours at room temperature, the reaction mixture is diluted with 240 ml of water and extracted with 100 ml of ethyl acetate. The aqueous phase is neutralized with 1.1 ml of concentrated hydrochloric acid and extracted with ethyl acetate. The extracts are dried over sodium sulfate and evaporated to an oil which is triturated with ether to give a semi-solid which is recrystallized from methanol to yield 3-(6-carboxyhex-1-enyl)-N-(3-pyridyl)indole, m.p. 124°-125°.

後処理

  1. waitAfter 18 hours at room temperature
  2. extractionextracted with 100 ml of ethyl acetate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extracts are dried over sodium sulfate
  5. customevaporated to an oil which
  6. customis triturated with ether
  7. customto give a semi-solid which
  8. customis recrystallized from methanol

出典と根拠

ORDレコード
ord-2dc8df6ce6464c01b10bdb1e35513d3e
出典データセット
uspto-grants-1985_08
特許番号
US04536505

反応ノート

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