Water → 1-[1-(Dibenzo[b,d]furan-2-yl)prop-1-en-1-yl]pyrrolidine

HRID 2049762Notes

Reaction equation

HRID 2049762 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.B(F)(F)F.[CH3:10][CH2:11][O:12][CH2:13][CH3:14].O.[C:16]1([CH3:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[CH:21]1[C:20]2[C:14]3[CH:2]=[CH:3][CH:4]=[CH:5][C:13]=3[O:12][C:11]=2[CH:10]=[CH:22][C:16]=1[C:17]([N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[CH:18][CH3:19]

Participants

5

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 8000Boron trifluoride etherateHCID 31268Pyrrolidine

Product 1

HCID 539019651-[1-(Dibenzo[b,d]furan-2-yl)prop-1-en-1-yl]pyrrolidineYield 34%

Procedure

In 100 ml of toluene, 2 g of the starting ketone, 2.12 g of pyrrolidine and 0.14 g of boron trifluoride etherate were dissolved. The mixture was refluxed for 47 hours under argon atmosphere using a Cope water separator and molecular sieve 4A as the dehydrating agent. After having distilled out the solvent, the residue was subjected to a distillation under a reduced pressure to obtain 0.95 g of the desired enamine (yield: 34%).

Workup

  1. temperatureThe mixture was refluxed for 47 hours under argon atmosphere
  2. distillationAfter having distilled out the solvent
  3. distillationthe residue was subjected to a distillation under a reduced pressure

Sources & evidence

ORD record
ord-85a2fb1f19d340cfa6a45f7136db4a65
Source dataset
uspto-grants-1980_04
Patent number
US04198510

Reaction notes

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