Diethyl Ether → HCID 67145279, compound

HRID 1750732Notes

Reaction equation

HRID 1750732 reaction equation
FC(F)(F)S(O[C:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14])(=O)=O.[Cl:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.C([O-])([O-])=O.[Na+].[Na+].CCOCC>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:23][CH:22]=1

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 394599Ethyl 2-[(trifluoromethanesulfonyl)oxy]cyclohex-1-ene-1-carboxylate

Product 1

HCID 67145279HCID 67145279, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of Example 8A (2.88 g, 10 mmol), 4-chlorophenylboronic acid (1.88 g, 12 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.578 g, 0.5 mmol) in toluene (40 ml) and ethanol (10 ml) was added 2N Na2CO3 (10 mL). The mixture was stirred at reflux overnight. The mixture was diluted ether (300 mL) and washed with water, brine and dried over Na2SO4. After evaporation of solvent, the residue was loaded on a column and eluted with 3% ethyl acetate in hexane to give title compound.

Workup

  1. temperatureat reflux overnight
  2. washwashed with water, brine
  3. dry with materialdried over Na2SO4
  4. customAfter evaporation of solvent
  5. washeluted with 3% ethyl acetate in hexane

Sources & evidence

ORD record
ord-cabf35ba1208474181a6f2984c588cc3
Source dataset
uspto-grants-2015_10
Patent number
US09156856B2

Reaction notes

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