Hydrochloric Acid → 5-[cyclohexyl-(4-methoxy-1H-indol-3-yl)-methyl]-2,2-dimethyl-[1,3]dioxane-4,6-dione

HRID 250201Notes

Reaction equation

HRID 250201 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5]([CH:12]=[C:13]1[C:18](=[O:19])[O:17][C:16]([CH3:21])([CH3:20])[O:15][C:14]1=[O:22])=[CH:6][NH:7]2.[CH:23]1([Mg]Br)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.[Cl-].[NH4+].Cl>C1COCC1>[CH:23]1([CH:12]([C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[CH:11][C:3]=3[O:2][CH3:1])[NH:7][CH:6]=2)[CH:13]2[C:18](=[O:19])[O:17][C:16]([CH3:20])([CH3:21])[O:15][C:14]2=[O:22])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 580886345-(4-methoxy-1H-indol-3-ylmethylene)-2,2-dimethyl-[1,3]dioxane-4,6-dioneHCID 178419651HCID 178419651, compound

Product 1

HCID 580884815-[cyclohexyl-(4-methoxy-1H-indol-3-yl)-methyl]-2,2-dimethyl-[1,3]dioxane-4,6-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(4-Methoxy-1H-indol-3-ylmethylene)-2,2-dimethyl-[1,3]dioxane-4,6-dione (0.392 g) was dissolved in dry THF (15 ml) and added slowly to cyclohexyl-magnesium bromide (10 ml, 1M) at room temperature with stirring. The reaction was stirred for 20 minutes, and then was worked up by the careful addition of saturated ammonium chloride solution, acidified with dilute HCl, and extracted with ethyl acetate. The crude product was purified on silica gel. Elution was done with 3:7 ethyl acetate-hexane to afford 0.390 g of 5-[cyclohexyl-(4-methoxy-1H-indol-3-yl)-methyl]-2,2-dimethyl-[1,3]dioxane-4,6-dione.

Workup

  1. stirringThe reaction was stirred for 20 minutes
  2. extractionextracted with ethyl acetate
  3. customThe crude product was purified on silica gel
  4. washElution

Sources & evidence

ORD record
ord-a578c8283a2d4f56a2dbec2049ad13bc
Source dataset
uspto-grants-2011_01
Patent number
US07863305B2

Reaction notes

Loading…