Ethoxalyl chloride → HCID 70855253、化合物

HRID 590977

反応式

HRID 590977 の反応式
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl[C:22](=[O:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:22](=[O:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:7]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

6

反応物 4

HCID 20884Ethoxalyl chlorideHCID 770951-Methyl-2-phenylindoleHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 70855253HCID 70855253、化合物収率 43%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

At 0° C., aluminum (III) chloride (2.5 g, 19 mmol) was added per portion to a solution of 1-methyl-2-phenyl-1H-indole (1 g, 4.8 mmol) and ethyl chlorooxoacetate (900 μL, 8.05 mmol) in dichloromethane (10 mL). The mixture was stirred for 2 hours at 0° C. and then hydrolyzed with a saturated solution of sodium bicarbonate. After removing the aqueous layer, organic layer was washed with water, brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10) to afford the desired keto-ester (8a) (630 mg, 2.05 mmol, 43%).

後処理

  1. customAfter removing the aqueous layer, organic layer
  2. washwas washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. 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-866331b423cb4203b3edccc029b13bb9
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…