Ethoxalyl chloride → HCID 70855253, compound

HRID 590977

Reaction equation

HRID 590977 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 70855253HCID 70855253, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-866331b423cb4203b3edccc029b13bb9
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Linked notes

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