Carbon Tetrachloride → HCID 22627276, compound

HRID 1108709Notes

Reaction equation

HRID 1108709 reaction equation
[CH2:1]([C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[C:8]([C:13]([O:15][CH3:16])=[O:14])[CH:7]=2)[CH2:2][CH3:3].[CH3:17][O:18][CH2:19][C:20](O)=[O:21].C(Cl)(Cl)(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCCl>[CH3:17][O:18][CH2:19][C:20]([C:12]1[C:11]2[C:6](=[CH:7][C:8]([C:13]([O:15][CH3:16])=[O:14])=[CH:9][CH:10]=2)[NH:5][C:4]=1[CH2:1][CH2:2][CH3:3])=[O:21]

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 12251Methoxyacetic AcidHCID 22627295Methyl 2-propylindole-6-carboxylate

Product 1

HCID 22627276HCID 22627276, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a mixture of methyl 2-propylindole-6-carboxylate (10 g), methoxyacetic acid (4.6 ml) and carbontetrachloride (13.4 ml) in 1,2-dichloroethane (45 ml) was added slowly triphenylphosphine (16.7 g) in 1,2-dichloroethane (30 ml) over 1 hour under reflux, and the resulting mixture was heated under reflux for additional 8 hours. After evaporation of solvent, the residue was chromatographed on silica gel eluting with a mixture of hexane and ethyl acetate (1:1) and triturated with diethyl ether to give methyl 3-methoxyacetyl-2-propylindole-6-carboxylate (8.11 g).

Workup

  1. temperatureunder reflux
  2. temperaturethe resulting mixture was heated
  3. temperatureunder reflux for additional 8 hours
  4. customAfter evaporation of solvent
  5. customthe residue was chromatographed on silica gel eluting with a mixture of hexane and ethyl acetate (1:1)
  6. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-5bbf5c1be77544b4b78e9a169a13bc68
Source dataset
uspto-grants-2000_05
Patent number
US06069156

Reaction notes

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