Ethoxalyl chloride → HCID 70855253, 화합물

HRID 590977

반응식

HRID 590977 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 70855253HCID 70855253, 화합물수율 43%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-866331b423cb4203b3edccc029b13bb9
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238026B2

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