Acetone → Acetone tetrahydrofuran

HRID 1805799Notes

Reaction equation

HRID 1805799 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 84.5%

Procedure

R,R′-atracurium besylate mixture (500 mg, isomer ratio −58:36:6) was placed in a 100 mL flask. 35 mL of THF was added to the solid followed by 3.5 mL of acetone. The mixture was stirred in an ice bath and HBF4 (48% in water, 200 μL) was added and the solution was stirred for 5 hours in the ice bath, during which time a white solid was formed. The slurry was filtered through a Buchner funnel to afford 244.6 mg (0.197 mmol, 84.5% yield from the cis isomer) of a white solid (isomer ratio −89:10.5:0.5).

Workup

  1. customwas formed
  2. filtrationThe slurry was filtered through a Buchner funnel
  3. customto afford 244.6 mg (0.197 mmol, 84.5% yield from the cis isomer) of a white solid (isomer ratio −89:10.5:0.5)

Sources & evidence

ORD record
ord-91a15d7f8c154353933e24bd903f7bcd
Source dataset
uspto-grants-2013_01
Patent number
US08354537B2

Reaction notes

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