Epichlorohydrin → 4-(2,3-Epoxypropoxy)-2-ethoxycarbonyl-6-methyl indole

HRID 903920Notes

Reaction equation

HRID 903920 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:6]2.[CH2:17]([CH:19]1[O:21][CH2:20]1)Cl>N1CCCCC1>[O:21]1[CH2:20][CH:19]1[CH2:17][O:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:6]2

Participants

4

Reactant 2

HCID 7835EpichlorohydrinHCID 233354994-Hydroxy-2-ethoxycarbonyl-6-methylindole

Product 1

HCID 205275294-(2,3-Epoxypropoxy)-2-ethoxycarbonyl-6-methyl indoleYield 64%

Reagents, catalysts & solvents 1

HCID 8082PiperidineCatalyst

Procedure

7.8 g of the thus obtained 4-hydroxy-2-ethoxycarbonyl-6-methylindole are dissolved in 100 ml epichlorohydrine and the solution is heated subsequent to the addition of 5 to 6 drops of piperidine, to boiling. After about 3 to 4 hours, the solution is evaporated in vacuum and the residue is recrystallized from isopropanol. There is obtained 6.4 g (~64% of theory) 4-(2,3-epoxypropoxy)-2-ethoxycarbonyl-6-methyl indole; m.p. 173°-175° C.

Workup

  1. customthe solution is evaporated in vacuum
  2. customthe residue is recrystallized from isopropanol

Sources & evidence

ORD record
ord-f4505958921a4f458dbaf237f2c1a071
Source dataset
uspto-grants-1980_10
Patent number
US04229464

Reaction notes

Loading…