Water → HCID 57175840, compound

HRID 2255260Notes

Reaction equation

HRID 2255260 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH2:11][C:10](=O)[CH2:9][CH2:8]2)([CH3:4])([CH3:3])[CH3:2].[NH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)[CH2:9][CH2:8]2)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 31268PyrrolidineHCID 21824008HCID 21824008, compound

Product 1

HCID 57175840HCID 57175840, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 6-t-butyl-2-tetralone (5.74 g; 28.37 mmol) in 100 ml of toluene was added 1.5 equiv. of pyrrolidine (3.56 ml; 42.56 mmol). A 100 mg portion of p-toluenesulfonic acid was added and the mixture was refluxed. The water eliminated during the reaction was collected by a Dean Stark trap. After a reflux time of 3.5 hours, concentration of the volatiles under vacuum afforded 7.31 g of the subtitle compound as a purple solid.

Workup

  1. temperaturethe mixture was refluxed
  2. customwas collected by a Dean Stark trap

Sources & evidence

ORD record
ord-9163261d54c64642b4126d1c700338b6
Source dataset
uspto-grants-1993_08
Patent number
US05239075

Reaction notes

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