Reaction #470369

ord-0b519d05882442eeb1c0ab17562a45fa

Reaction equation

O=S(=O)(O)C(F)(F)F
trifluoromethanesulfonic acid
COC[N+]1(C)CCCC1.[Cl-]
N-methoxymethyl-N-methylpyrrolidinium chloride
COC[N+]1(C)CCCC1.[Cl-]
N-Methoxymethyl-N-Methylpyrrolidinium Chloride
→
O=S(=O)(O)C(F)(F)F
trifluoromethanesulfonic acid
COC[N+]1(C)CCCC1
desired product
COC[N+]1(C)CCCC1
N-Methoxymethyl-N-Methylpyrrolidinium

Reactants

O=S(=O)(O)C(F)(F)F
trifluoromethanesulfonic acid
COC[N+]1(C)CCCC1.[Cl-]
N-methoxymethyl-N-methylpyrrolidinium chloride
COC[N+]1(C)CCCC1.[Cl-]
N-Methoxymethyl-N-Methylpyrrolidinium Chloride

Reagents

None

Solvents

CO
methanol
CO
methanol
CO
MeOH

Conditions

Temperature
130°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherto remove hydrogen chloride
  2. 2
    Otherproduced as a by-product

Procedure

A 30.0 g quantity of N-methoxymethyl-N-methylpyrrolidinium chloride prepared in Example 10 was dissolved in 30.0 g of MeOH, and 80.0 g of methanol solution of 35 wt. % trifluoromethanesulfonic acid was added to the solution. The mixture was heated at 130° C. in a nitrogen stream to remove hydrogen chloride produced as a by-product, an excess of trifluoromethanesulfonic acid and methanol, giving 49.0 g of the desired product.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08366956B2uspto-grants-2013_02