Methanol → HCID 18946729, compound

HRID 1769204Notes

Reaction equation

HRID 1769204 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH2:5]([C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][C:12]=2[C:18]([O:20][CH3:21])=[O:19])[CH2:6][CH2:7][CH3:8].[CH3:22][OH:23].O>C1(C)C=CC=CC=1.ClCCl>[CH2:5]([C:9]1[NH:10][C:11]2[C:16]([C:17]=1[C:22]([O:2][CH3:1])=[O:23])=[CH:15][CH:14]=[CH:13][C:12]=2[C:18]([O:20][CH3:21])=[O:19])[CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 6371PhosgeneHCID 18946596HCID 18946596, compound

Product 1

HCID 18946729HCID 18946729, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of phosgene in toluene (37 ml, 1.9M) was added to a solution of methyl 2-(n-butyl)indole-7-carboxylate (32) (11.5 g) (prepared, e.g., as described in Preparation 21), at 5° C. in dichloromethane (75 ml). The solution was stirred at room temperature for 16 hours, cooled in an ice bath, and treated with methanol (20 ml). Water was added, and the dichloromethane layer was separated and solvent evaporated under reduced pressure. Chromatography on silica gel, eluting with 20% ethyl acetate/hexane, afforded dimethyl 2-(n-butyl)indole-3,7-dicarboxylate (7.4 g), a compound of Formula (33), as an oil.

Workup

  1. temperaturecooled in an ice bath
  2. customthe dichloromethane layer was separated
  3. customsolvent evaporated under reduced pressure
  4. washChromatography on silica gel, eluting with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-30b6d483654649d1993b8a38d25b93fa
Source dataset
uspto-grants-1995_01
Patent number
US05380739

Reaction notes

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