Ethylene Glycol → 5'-Cyclohexyl-spiro[1,3-dioxolane-2,3'-[3H]-indol]-2'(1'H)-one

HRID 1081275Notes

Reaction equation

HRID 1081275 reaction equation
[CH:1]1([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][C:11](=[O:16])[C:10]3=[O:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:18](O)[CH2:19][OH:20].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH:1]1([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][C:11](=[O:16])[C:10]23[O:20][CH2:19][CH2:18][O:17]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 125119305-Cyclohexylindoline-2,3-dione

Product 1

HCID 233638615'-Cyclohexyl-spiro[1,3-dioxolane-2,3'-[3H]-indol]-2'(1'H)-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-Cyclohexyl-1H-indole-2,3-dione (1 equivalent), ethane-1,2-diol (5 equivalents) and p-toluenesulphonic acid (0.02 equivalents) in dry toluene were heated under reflux overnight with azeotropic removal of water. The reaction mixture was cooled, washed with saturated sodium bicarbonate solution, and then worked up in the usual manner to afford the title compound.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with saturated sodium bicarbonate solution

Sources & evidence

ORD record
ord-3c387fdbf95f42d7ba2534beed0427e5
Source dataset
uspto-grants-1996_12
Patent number
US05585378

Reaction notes

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