Hydrochloric Acid → Ethyl 3-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-hydroxy-1H-indol-2-yl)-2,2-dimethylpropanoate

HRID 1609219Notes

Reaction equation

HRID 1609219 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:37]=[CH:36][C:9]([CH2:10][N:11]2[C:19]3[C:14](=[CH:15][C:16]([O:20]C)=[CH:17][CH:18]=3)[C:13]([S:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[C:12]2[CH2:27][C:28]([CH3:35])([CH3:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:8][CH:7]=1.Cl>C(S)(C)(C)C.C(Cl)Cl>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:10][N:11]2[C:19]3[C:14](=[CH:15][C:16]([OH:20])=[CH:17][CH:18]=3)[C:13]([S:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[C:12]2[CH2:27][C:28]([CH3:35])([CH3:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:36][CH:37]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 19935666Ethyl 3-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-methoxy-1H-indol-2-yl)-2,2-dimethylpropanoate

Product 1

HCID 19935664Ethyl 3-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-hydroxy-1H-indol-2-yl)-2,2-dimethylpropanoateYield 69.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6387tert-Butyl mercaptanSolvent

Procedure

To a suspension of aluminum chloride (26.3 g, 198 mmol) in t-butanethiol (60 ml) at 0° C. was added a solution of ethyl 3-(1-(4-chlorobenzyl)-3-(t-butylthio)-5-methoxyindol-2-yl)-2,2-dimethylpropionate (32 g, 66 mmol), prepared as in step 2, in methylene chloride (90 ml) and the reaction mixture was stirred at 0° C. for 10 min and at ambient temperature for 3 hours. The reaction mixture was then poured into ice and acidified with 10% aqueous hydrochloric acid. The organic layer was washed with water and brine, dried over MgSO4, filtered, and concentrated in vacuo to provide a white solid. The solid was washed with 20% solution of ethyl ether in hexane and dried in vacuo to afford 21.8 g of ethyl 3-(1-(4-chlorobenzyl)-3-(t-butylthio)-5-hydroxyindol-2-yl)-2,2-dimethylpropionate.

Workup

  1. additionwas added
  2. additionThe reaction mixture was then poured into ice
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto provide a white solid
  8. washThe solid was washed with 20% solution of ethyl ether in hexane
  9. customdried in vacuo

Sources & evidence

ORD record
ord-5b491cb31f3f43d28df96a3d78bfeb75
Source dataset
uspto-grants-1995_03
Patent number
US05399699

Reaction notes

Loading…