Sodium Carbonate → (E)-2-[4-(3-Benzyloxy-propylsulfanyl)-phenyl]-3-cyclopentyl-acrylic acid ethyl ester

HRID 2103598Notes

Reaction equation

HRID 2103598 reaction equation
C([O-])(=O)C.[K+].CC1(C)C(C)(C)OB(B2OC(C)(C)C(C)(C)O2)O1.[CH2:24]([O:31][CH2:32][CH2:33][CH2:34][S:35][C:36]1[CH:41]=[CH:40][C:39](Br)=[CH:38][CH:37]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[CH2:43]([O:45][C:46](=[O:55])/[C:47](/Br)=[CH:48]/[CH:49]1[CH2:53][CH2:52][CH2:51][CH2:50]1)[CH3:44].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>[CH2:43]([O:45][C:46](=[O:55])/[C:47](/[C:39]1[CH:40]=[CH:41][C:36]([S:35][CH2:34][CH2:33][CH2:32][O:31][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:37][CH:38]=1)=[CH:48]/[CH:49]1[CH2:53][CH2:52][CH2:51][CH2:50]1)[CH3:44]

Participants

9

Reactant 5

HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 670847241-(3-Benzyloxy-propylsulfanyl)-4-bromo-benzeneHCID 86605124(Z)-2-bromo-3-cyclopentyl-acrylic acid ethyl ester

Product 1

HCID 67084463(E)-2-[4-(3-Benzyloxy-propylsulfanyl)-phenyl]-3-cyclopentyl-acrylic acid ethyl esterYield 178.4%

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 (1.7 g, 17.3 mmol), 4,4,5,5,4′,4′,5′,5′-octamethyl-[2,2′]bi[[1,3,2]dioxaborolanyl] (1.6 g, 6.35 mmol) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (424 mg, 0.58 mmol) to a solution of 1-(3-benzyloxy-propylsulfanyl)-4-bromo-benzene (1.95 g, 5.77 mmol) in 15 mL DMF and stir 1 hour at 80° C. Then add (Z)-2-bromo-3-cyclopentyl-acrylic acid ethyl ester (2.85 g, 11.54 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (424 mg, 0.58 mmol) and sodium carbonate solution (2 M, 14.0 mL, 28.0 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 dichloromethane affords the title compound as yellow oil (4.37 g). MS (m/e): 425 (M+H).

Workup

  1. filtrationfilter
  2. washWash with water and brine
  3. filtrationfilter through a hydrophobic filter paper
  4. concentrationconcentrate
  5. customFurther purification via silica gel column chromatography
  6. washeluting with dichloromethane

Sources & evidence

ORD record
ord-6f5a1d03b2c84c9e8b74a6b65143df2b
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

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