3,4-dihydro-2H-pyran → 3-(5-chloro-1H-indol-3-yl)propan-1-ol

HRID 1918538

反応式

HRID 1918538 の反応式
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1>O.O1CCOCC1.C(OCC)(=O)C>[Cl:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][CH:4]=1)[NH:9][CH:16]=[C:15]2[CH2:14][CH2:13][CH2:12][OH:11]

参加物

6

反応物 2

HCID 80803,4-dihydro-2H-pyranHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)

生成物 1

HCID 199793473-(5-chloro-1H-indol-3-yl)propan-1-ol収率 64.4%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A mixture of (4-chlorophenyl)hydrazine hydrochloride (5.26 g; 28.50 mmol) and 3,4-dihydro-2H-pyran (2.63 mL; 28.50 mmol) in a mixture of water (9 mL) and dioxane (36 mL) was stirred at 100° C. for 48 hours. After cooling to room temperature the mixture was diluted with ethyl acetate. The aqueous layer was separated and further extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluent: 0 to 6% methanol in dichloromethane) to afford 3.85 g (64%) of 3-(5-chloro-1H-indol-3-yl)propan-1-ol as an oily residue.

後処理

  1. temperatureAfter cooling to room temperature the mixture
  2. customThe aqueous layer was separated
  3. extractionfurther extracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (eluent: 0 to 6% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-2784cdb7b2824ccfabe6f728c75089fb
出典データセット
uspto-grants-2013_12
特許番号
US08618138B2

関連ノート

読み込み中…