Hydrochloric Acid → 2,2,2-trifluoro-1,1-bis(1H-pyrrol-2-yl)ethane

HRID 1899387Notes

Reaction equation

HRID 1899387 reaction equation
N1C=CC=C1.COC(O)[C:9]([F:12])([F:11])[F:10].Cl.[CH:15]1[CH:19]=[C:18]([CH2:20][C:21]2[NH:25][CH:24]=[CH:23][CH:22]=2)[NH:17][CH:16]=1>O1CCCC1>[NH:25]1[CH:24]=[CH:23][CH:22]=[C:21]1[CH:20]([C:18]1[NH:17][CH:16]=[CH:15][CH:19]=1)[C:9]([F:12])([F:11])[F:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8027PyrroleHCID 98922,2,2-Trifluoro-1-methoxyethanolHCID 140814Dipyrromethane

Product 1

HCID 98157622,2,2-trifluoro-1,1-bis(1H-pyrrol-2-yl)ethaneYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Pyrrole (150 mmol) and trifluoroacetaldehyde methyl hemiacetal (75 mmol) in tetrahydrofuran are heated at reflux with catalytic amounts of hydrochloric acid for 2 hours under an inert atmosphere. GC analysis of the reaction mixture indicated the presence of the desired dipyrromethane in greater than 80% yield. Neutralization of the acid followed by work up and chromatography gave the pure bis(pyrrol-2-yl)-trifluoromethylmethane 3 (R3 =CF3)). MS:m/z=214. This preparation has been disclosed in Wijesekera U.S. patent application Ser. No. 08/143,261 filed on Oct. 26, 1993.

Sources & evidence

ORD record
ord-0ca8fa0d0681414b926d5fe8f4eabd1e
Source dataset
uspto-grants-1996_11
Patent number
US05571908

Reaction notes

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