3-Dipropylamino-5-chloroformyichroman → 3-Dipropylamino-5-acetylchroman

HRID 37649ノート

反応式

HRID 37649 の反応式
[CH2:1]([N:4]([CH2:18][CH2:19][CH3:20])[CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[C:15](Cl)=[O:16])[O:7][CH2:6]1)[CH2:2][CH3:3].[CH2:21](N(CCC)C1CC2C(=CC=CC=2C(OC)=O)OC1)CC.[Li]C>O1CCCC1.[Cu]I>[CH2:1]([N:4]([CH2:18][CH2:19][CH3:20])[CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[C:15](=[O:16])[CH3:21])[O:7][CH2:6]1)[CH2:2][CH3:3]

参加物

6

反応物 3

HCID 190280843-Dipropylamino-5-chloroformyichromanHCID 190280933-Dipropylamino-5-methyloxycarbonylchromanHCID 178418348HCID 178418348、化合物

生成物 1

HCID 102212133-Dipropylamino-5-acetylchroman

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

3-Dipropylamino-5-chloroformylchroman*HCl (4.42 g, 13.4 mmol), prepared from 3-dipropylamino-5-methyloxycarbonylchroman (Example 2) analogous to the procedure used in Example 3, in dry tetrahydrofuran (20 ml), was added to a pre-formed solution of lithium dimethylcuprate; prepared from MeLi and CuI, in 200 mL tetrahydrofuran at -78° C. The solution was stirred for 15 minutes at -78° C. and was then allowed to reach room temperature during 10 minutes. Then, 30 mL H20 was slowly added. The organic phase was decanted, dried with Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (silica gel) by elution with ethyl acetate/hexane 1:8. The title compound was crystallized as salt from ethyl acetate. Mp 106°-108° C. (oxalate).

後処理

  1. waitto reach room temperature during 10 minutes
  2. additionThen, 30 mL H20 was slowly added
  3. customThe organic phase was decanted
  4. dry with materialdried with Na2SO4
  5. customevaporated to dryness
  6. customThe residue was purified by flash chromatography (silica gel) by elution with ethyl acetate/hexane 1:8
  7. customThe title compound was crystallized as salt from ethyl acetate

出典と根拠

ORDレコード
ord-be46729521be46dc9b9e591301f42c4d
出典データセット
uspto-grants-1995_05
特許番号
US05420151

反応ノート

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