Methanol → HCID 19995020, compound

HRID 2248775Notes

Reaction equation

HRID 2248775 reaction equation
[OH2:1].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:13][O:14][CH:15]=[CH:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[N:22]([CH2:26][CH2:27][CH3:28])[CH:21]=[C:20]2[CH2:29][C:30]1[CH:39]=[CH:38][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:32][C:31]=1[O:40][CH3:41].[CH3:42]O>C(Cl)Cl>[CH3:13][O:14][CH:15]([O:1][CH3:42])[CH2:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[N:22]([CH2:26][CH2:27][CH3:28])[CH:21]=[C:20]2[CH2:29][C:30]1[CH:39]=[CH:38][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:32][C:31]=1[O:40][CH3:41]

Participants

5

Reactant 3

HCID 887MethanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 57325365Methyl 4-[5-(2-methoxyvinyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate

Product 1

HCID 19995020HCID 19995020, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

para-Toluenesulfonic acid hydrate (0.55 g) was added to a stirred solution of methyl 4-[5-(2-methoxyvinyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate (0.2 g) in 1:1 methanol:methylene chloride (5 ml), under a nitrogen atmosphere. After 4 h, the mixture was evaporated at ambient temperature, and the product was purified by flash chromatography, eluting with 4:1 hexane:ethyl acetate, to give methyl 4-[5-(2,2-dimethoxyethyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate (0.19 g, 88%) as an oil; partial NMR (300 MHz, DMSO-d6): 0.81(t, 3H, CH3), 1.71(m, 2H, CH2), 2.84(m, 2H, CH2), 3.20(s, 6H, 2xOCH3), 3.83(s, 3H, OCH3), 3.91(s, 3H, OCH3), 4.02(m, 4H, NCH2, ArCH2Ar'), 4.50(t, 1H, CH).

Workup

  1. customthe mixture was evaporated at ambient temperature
  2. customthe product was purified by flash chromatography
  3. washeluting with 4:1 hexane

Sources & evidence

ORD record
ord-f044f60f2e3f41b58df3fff3df20062b
Source dataset
uspto-grants-1991_08
Patent number
US05041460

Reaction notes

Loading…