Acetone → Acetone tetrahydrofuran

HRID 1805801Notes

Reaction equation

HRID 1805801 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[H+].[B-](F)(F)(F)F.[CH3:12][C:13]([CH3:15])=[O:14]>>[CH2:4]1[CH2:5][O:1][CH2:2][CH2:3]1.[CH3:12][C:13]([CH3:15])=[O:14]

Participants

4

Reactant 3

HCID 180AcetoneHCID 8028TetrahydrofuranHCID 28118Tetrafluoroboric acid

Product 1

HCID 22559816Acetone tetrahydrofuranYield 41.9%

Procedure

Crude R,R′-atracurium tetrafluoroborate (244.6 mg, isomer ratio −89:10.5:0.5) was placed in a 50 mL flask. 17 mL of THF followed by 1.7 mL of acetone were added to the white solid. The reaction mixture was stirred in an ice bath and HBF4 (48% in water, 40 μL) was added and the slurry was stirred for 5 hours in the ice bath. The slurry was filtered through a Buchner funnel to afford 90.1 mg (0.0725 mmol, 41.9% yield from the cis isomer) of a white solid having 93:7:0 isomer ratio.

Workup

  1. additionwere added to the white solid
  2. filtrationThe slurry was filtered through a Buchner funnel
  3. customto afford 90.1 mg (0.0725 mmol, 41.9% yield from the cis isomer) of a white solid

Sources & evidence

ORD record
ord-cac918135c0e454e9f2d83ac7026185f
Source dataset
uspto-grants-2013_01
Patent number
US08354537B2

Reaction notes

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