Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1) → HCID 54228902, compound

HRID 75120Notes

Reaction equation

HRID 75120 reaction equation
[O:1]1[CH:7]=[CH:6][CH:5]=[N:4][C:3](=[O:8])[CH2:2]1.F[B-](F)(F)F.[CH3:14][O+](C)C>C(Cl)Cl>[CH3:14][O:8][C:3]1[CH2:2][O:1][CH2:7][CH2:6][CH2:5][N:4]=1

Participants

4

Reactant 2

HCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 536461591,4-Oxazepine-3-one

Product 1

HCID 54228902HCID 54228902, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from step 4 (1.06 g, 9.2 mmol) was dissolved in 11 mL of DCM and the stirred solution was treated with trimethyloxonium tetrafluoroborate (1.70 g, 11.5 mmol) and the mixture was stirred for 4 hours. The reaction was quenched by addition of 1.70 mL saturated aqueous K2CO3 and the mixture was vigorously stirred for 15 minutes. The precipitate was removed by filtration and the filtrate concentrated in vacuo to provide 3-methoxy-2,5,6,7-tetrahydro-1,4-oxazepine (0.94 g, 80%) as a clear oil that was used without further purification.

Workup

  1. customThe reaction was quenched by addition of 1.70 mL saturated aqueous K2CO3
  2. stirringthe mixture was vigorously stirred for 15 minutes
  3. customThe precipitate was removed by filtration
  4. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-a6e58ccf17d14ce0bfebae563c768f00
Source dataset
uspto-grants-2014_09
Patent number
US08835422B2

Reaction notes

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