Water → ethyl 2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)acrylate

HRID 2192890Notes

Reaction equation

HRID 2192890 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:14](=[CH:20][CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:5]=[CH:6][C:7]=1[S:8]([CH:11]1[CH2:13][CH2:12]1)(=[O:10])=[O:9].[CH:27]1(B(O)O)[CH2:29][CH2:28]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>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.C(OCC)(=O)C>[CH:27]1([C:2]2[CH:3]=[C:4]([C:14](=[CH:20][CH:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:5]=[CH:6][C:7]=2[S:8]([CH:11]2[CH2:13][CH2:12]2)(=[O:10])=[O:9])[CH2:29][CH2:28]1

Participants

8

Reactant 4

HCID 962Water2×HCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 68671424ethyl 2-[3-bromo-4-(cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)acrylate

Product 1

HCID 68670876ethyl 2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)acrylateYield 81.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Ethyl 2-[3-bromo-4-(cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)acrylate (4.72 g), cyclopropylboronic acid (1.37 g), and tetrakis(triphenylphosphine)palladium (615 mg) were dissolved in toluene (142 mL), and to this solution were added tripotassium phosphate (4.07 g, 19.2 mmol) and water (7.1 mL). The mixture was stirred at 100° C. for 20 hours. It was cooled to room temperature, and water and ethyl acetate were added thereto. The organic layer was separated, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and then dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the obtained residue was purified by silica gel column chromatography to obtain ethyl 2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)acrylate (3.50 g) as an (E)/(Z)-mixture of olefin.

Workup

  1. temperatureIt was cooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationAfter concentration under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-843b5ac227bf409d9c34beb97099352d
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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