Methanol → 2-Methoxypyrrolidine-1-carbaldehyde

HRID 1111674

Reaction equation

HRID 1111674 reaction equation
[CH:1]([N:3]1[CH2:7][CH2:6][CH2:5][CH2:4]1)=[O:2].[CH3:8][OH:9]>F[B-](F)(F)F.C[N+](C)(C)C>[CH:1]([N:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[O:9][CH3:8])=[O:2]

Participants

4

Reactant 2

HCID 887MethanolHCID 773721-Pyrrolidinecarboxaldehyde2×

Product 1

HCID 124781712-Methoxypyrrolidine-1-carbaldehydeYield 86.7%

Reagents, catalysts & solvents 1

HCID 12621Tetramethylammonium tetrafluoroborateCatalyst

Procedure

In the same manner as indicated in Example 5 there are electrolyzed 17.7 g of N-formylpyrrolidine and 57.2 g of methanol in the presence of 0.29 g of tetramethylammonium tetrafluoroborate as conducting salt. In this case, however, the current is switched off after the throughput of already 2.0 Faraday per mol of N-formylpyrrolidine. The calculated mean cell voltage is 28.8 volts. Work-up of the electrolysis solution gives 20.0 g of 1-formyl-2-methoxypyrrolidine (boiling point 39°-40° C./0.1 mbar; nD25 = 1.4700), which corresponds to a product yield of 86.6% and a current efficiency of 86.6%.

Sources & evidence

ORD record
ord-45fd67c55a7141f880258e2316a7201c
Source dataset
uspto-grants-1978_10
Patent number
US04118500

Linked notes

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