Water → HCID 57941052, compound

HRID 1437366Notes

Reaction equation

HRID 1437366 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][C:9]([O:12][Si](C)(C)C)=[CH:8][CH2:7]1)=[O:5])[CH3:2].[B-](F)(F)(F)[F:18].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1.C(=O)([O-])O.[Na+].O>C(#N)C>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][C:9](=[O:12])[C@@H:8]([F:18])[CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 2724933SelectfluorHCID 57941061HCID 57941061, compound

Product 1

HCID 57941052HCID 57941052, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Silyl enol ether (a) (3.5 g) in acetonitrile (40 mL) at 0° C. was treated portionwise with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octanebis(tetrafluoroborate), (Selectfluor™), (6.16 g). After 75 min, saturated sodium hydrogen carbonate (50 mL) and water (50 mL) were added and the mixture extracted with ethyl acetate. The organic soluble material was purified by careful chromatography on silica gel eluting with 5-60% diethyl ether in hexane to give an oil (1.02 g).

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. customThe organic soluble material was purified by careful chromatography on silica gel eluting with 5-60% diethyl ether in hexane

Sources & evidence

ORD record
ord-5a2cbd6910e1452ab182b0070aa9deb4
Source dataset
uspto-grants-2009_11
Patent number
US07622481B2

Reaction notes

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