Phenylacetaldehyde → 3-Phenylindole

HRID 590952

反応式

HRID 590952 の反応式
[C:1]1([NH:7]N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]1([CH2:15][CH:16]=O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C>[C:9]1([C:15]2[C:6]3[C:1](=[CH:2][CH:3]=[CH:4][CH:5]=3)[NH:7][CH:16]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

5

反応物 3

HCID 998PhenylacetaldehydeHCID 7516PhenylhydrazineHCID 10340Sodium Carbonate

生成物 1

HCID 965023-Phenylindole収率 48%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A solution of phenylhydrazine (1 mL, 10.15 mmol) and phenylacetaldehyde (1.32 mL, 10.15 mmol) in acetic acid was refluxed for 6 hours under a nitrogen atmosphere. After cooling to room temperature, the reaction mixture was poured into a saturated aqueous solution of sodium carbonate (100 mL) at 0° C. After extraction with dichloromethane (2×30 mL), the organic layer was dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10) to afford the desired indole (1a) as a pale oil (940 mg, 4.86 mmol, 48%).

後処理

  1. extractionAfter extraction with dichloromethane (2×30 mL)
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10)

出典と根拠

ORDレコード
ord-7e43f1a3e5394584957a94950323f391
出典データセット
uspto-grants-2016_01
特許番号
US09238026B2

関連ノート

読み込み中…