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Dichloromethane → 1,2,3-Trimethyl-3-phenyl-1,2-methylene pyrrolidinium tetrafluoroborate

HRID 1764120
Notes
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Reaction equation

HRID 1764120 reaction equation
[F:1][B-:2]([F:5])([F:4])[F:3].[CH3:6][N+:7]1[CH2:11][CH2:10][C:9]([CH3:18])([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]=1[CH3:19].Cl[CH2:21]Cl.[N+](=C)=[N-]>C(OCC)C>[F:1][B-:2]([F:5])([F:4])[F:3].[CH3:6][N+:7]12[CH2:19][C:8]1([CH3:21])[C:9]([CH3:18])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:10][CH2:11]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 9550DiazomethaneHCID 203486051,2,3-Trimethyl-3-phenyl-1-pyrrolinium tetrafluoroborate

Product 1

HCID 203486641,2,3-Trimethyl-3-phenyl-1,2-methylene pyrrolidinium tetrafluoroborate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 17 g. of 1,2,3-trimethyl-3-phenyl-1-pyrrolinium tetrafluoroborate in 400 cc. of dichloromethane was stirred and cooled to 0° C. in an ice-water bath. A solution of diazomethane in diethyl ether was added dropwise to the reaction mixture over 21/2 hours. The reaction mixture was warmed to 25° C. and stirred for 12 hours. The solvent was evaporated from the reaction mixture under reduced pressure to provide 1,2,3-trimethyl-3-phenyl-1,2-methylene pyrrolidinium tetrafluoroborate as a solid. M.P. 151°-155° C.

Workup

  1. temperatureThe reaction mixture was warmed to 25° C.
  2. customThe solvent was evaporated from the reaction mixture under reduced pressure

Sources & evidence

ORD record
ord-fc8c4be3ab634542999845fab7ed4f7d
Source dataset
uspto-grants-1978_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04115400

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes