Ethanol → HCID 57827608, compound

HRID 1842173Notes

Reaction equation

HRID 1842173 reaction equation
C(O)C.FC(F)(F)S(O[C:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17])(=O)=O.[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.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>[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 394599Ethyl 2-[(trifluoromethanesulfonyl)oxy]cyclohex-1-ene-1-carboxylateHCID 27343542-Fluorophenylboronic acid

Product 1

HCID 57827608HCID 57827608, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Ethanol (100 mL) was added to a solution of ethyl 2-trifluoromethanesulfonyloxycyclohex-1-enecarboxylate obtained in Preparation Example 1-(1) (17.0 g) in toluene (200 mL). 2-Fluorophenylboronic acid (7.74 g) and tetrakis(triphenylphosphine)palladium (1.60 g) were added. A 1 N sodium carbonate solution (55.3 mL) was added, followed by replacement of the reaction atmosphere with nitrogen. The reaction solution was heated to 80° C. and stirred for eight hours. After returning to room temperature, the excess of ethanol was evaporated under reduced pressure and the residue was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (10.5 g).

Workup

  1. customfollowed by replacement of the reaction atmosphere with nitrogen
  2. customAfter returning to room temperature
  3. customthe excess of ethanol was evaporated under reduced pressure
  4. extractionthe residue was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customThe drying agent was removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-784f5cdba0444f36ae4bd76161f429c4
Source dataset
uspto-grants-2015_02
Patent number
US08946210B2

Reaction notes

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