Sodium Carbonate → (E)-3-Cyclohexyl-2-(4-methanesulfonyl-3-trifluoromethoxy-phenyl)-prop-2-en-1-ol

HRID 2103640Notes

Reaction equation

HRID 2103640 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[C:4]([O:12][C:13]([F:16])([F:15])[F:14])[CH:3]=1.[CH:17]1(/[CH:23]=[C:24](\B2OC(C)(C)C(C)(C)O2)/[CH2:25][OH:26])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.C(OCC)(=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]>[CH:17]1(/[CH:23]=[C:24](\[C:2]2[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[C:4]([O:12][C:13]([F:16])([F:15])[F:14])[CH:3]=2)/[CH2:25][OH:26])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 534180354-Bromo-1-methanesulfonyl-2-(trifluoromethoxy)benzeneHCID 67084598(E)-3-cyclohexyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol

Product 1

HCID 67484942(E)-3-Cyclohexyl-2-(4-methanesulfonyl-3-trifluoromethoxy-phenyl)-prop-2-en-1-olYield 88.9%

Reagents, catalysts & solvents 3

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

Procedure

Heat a suspension of 4-bromo-1-methanesulfonyl-2-trifluoromethoxy-benzene (0.71 g, 2.23 mmol), (E)-3-cyclohexyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol (0.77 g, 2.91 mmol), 2 M aqueous sodium carbonate solution (2.2 mL, 4.4 mmol) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (164 mg, 2.13 mmol) in 5.7 mL DMF to 80° C. for 2 h. Dilute the mixture with ethyl acetate, separate the organic layer, wash it with water followed by saturated sodium chloride solution. Filter through a hydrophobic filter paper and remove the solvent under vacuum. Further purify the resulting residue by column chromatography, eluting with a gradient from 100:0 to 30:70 hexanes:ethyl acetate to afford the title compound (0.75 g) as a yellow oil. MS (m/e): 396 (M+4H2O).

Workup

  1. temperatureHeat
  2. customseparate the organic layer
  3. washwash it with water
  4. filtrationFilter through a hydrophobic filter paper
  5. customremove the solvent under vacuum
  6. customFurther purify the resulting residue by column chromatography
  7. washeluting with a gradient from 100:0 to 30:70 hexanes

Sources & evidence

ORD record
ord-1a2a8bdadc444bc59f0351783204bd50
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

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