Sodium Bicarbonate → 4'-(Fluoro)flavanone

HRID 571453Notes

Reaction equation

HRID 571453 reaction equation
FC(F)(F)S([C:6]1[CH:22]=[CH:21][C:9]([CH:10]2[CH2:19][C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[O:11]2)=[CH:8][CH:7]=1)(=O)=O.C(=O)(O)[O-].[Na+].[F:30]C(F)(F)S([O-])(=O)=O.[Na+].F[P-](F)(F)(F)(F)F.F[P-](F)(F)(F)(F)F.ClC[N+]12CC[N+](F)(CC1)CC2>CC(C)=O.[Ag]=O>[F:30][C:6]1[CH:22]=[CH:21][C:9]([CH:10]2[CH2:19][C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[O:11]2)=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 10719166HCID 10719166, compoundHCID 23676748Sodium trifluoromethanesulfonateHCID 67424417HCID 67424417, compound

Product 1

HCID 110320584'-(Fluoro)flavanoneYield 90%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 180AcetoneSolvent

Conditions

Temperature
65 °C

Procedure

To 4′-(Trifluoromethanesulfonyl)flavanone (51.4 mg, 0.100 mmol, 1.00 equiv) in acetone (2.0 mL) at 23° C. was added silver oxide (1.16 mg, 0.00500 mmol, 0.05 equiv), sodium bicarbonate (16.8 mg, 0.200 mmol, 2.00 equiv), sodium trifluoromethanesulfonate (17.2 mg, 0.100 mmol, 1.00 equiv) and 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(hexafluorophosphate) (2) (70.5 mg, 0.150 mmol, 1.50 equiv). The reaction mixture was stirred for 5 h at 65° C. in a sealed vial, then cooled to 23° C. and concentrated in vacuo. The residue was purified by preparative TLC with hexane/EtOAc 5:1 (v/v) to afford 21.8 mg of the title compound as a white solid (90% yield).

Workup

  1. temperaturethen cooled to 23° C.
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by preparative TLC with hexane/EtOAc 5:1 (v/v)

Sources & evidence

ORD record
ord-37709adf6fae437e9ceee66e2eda6c77
Source dataset
uspto-grants-2015_05
Patent number
US09024093B2

Reaction notes

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