Sodium Carbonate → (E)-3-Cyclohexyl-2-(4-isopropylsulfanyl-phenyl)-acrylic acid ethyl ester

HRID 2103602Notes

Reaction equation

HRID 2103602 reaction equation
C([O-])(=O)C.[K+].CC1(C)C(C)(C)OB(B2OC(C)(C)C(C)(C)O2)O1.Br[C:25]1[CH:30]=[CH:29][C:28]([S:31][CH:32]([CH3:34])[CH3:33])=[CH:27][CH:26]=1.[CH2:35]([O:37][C:38](=[O:48])/[C:39](/Br)=[CH:40]/[CH:41]1[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1)[CH3:36].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(OCC)(=O)C>[CH2:35]([O:37][C:38](=[O:48])/[C:39](/[C:25]1[CH:30]=[CH:29][C:28]([S:31][CH:32]([CH3:34])[CH3:33])=[CH:27][CH:26]=1)=[CH:40]/[CH:41]1[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1)[CH3:36]

Participants

9

Reactant 5

HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 125212401-Bromo-4-(propan-2-ylsulfanyl)benzeneHCID 21575668(Z)-Ethyl 2-bromo-3-cyclohexylacrylate

Product 1

HCID 67084393(E)-3-Cyclohexyl-2-(4-isopropylsulfanyl-phenyl)-acrylic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst2×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Add potassium acetate (2.5 g, 26 mmol), 4,4,5,5,4′,4′,5′,5′-octamethyl-[2,2′]bi[[1,3,2]dioxaborolanyl] (2.42 g, 9.52 mmol) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (629 mg, 0.86 mmol) to a solution of 1-bromo-4-isopropylsulfanyl-benzene (2.0 g, 8.65 mmol) in 30 mL DMF and stir 2 hour at 80° C. Then add (Z)-2-bromo-3-cyclohexyl-acrylic acid ethyl ester is (4.5 g, 17.3 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (629 mg, 0.86 mmol) and sodium carbonate solution (2 M, 21.0 mL, 42.0 mmol) and stir at 80° C. over night. Add 100 mL ethyl acetate and filter. Wash with water and brine, filter through a hydrophobic filter paper and concentrate. Further purification via silica gel column chromatography, eluting with a gradient from 100:0 to 98:2 hexane:ethyl acetate affords the title compound as yellow oil (1.25 g). MS (m/e): 333 (M+H).

Workup

  1. stirringstir at 80° C. over night
  2. filtrationfilter
  3. washWash with water and brine
  4. filtrationfilter through a hydrophobic filter paper
  5. concentrationconcentrate
  6. customFurther purification via silica gel column chromatography
  7. washeluting with a gradient from 100:0 to 98:2 hexane

Sources & evidence

ORD record
ord-6f2968485da543bfb8e9ec5c803ace94
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

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