Ethyl Acetate → 5(R)-(4-{1-[3'-(2,2-dimethyl-1-trimethylsilanyloxy-propyl)-2-methyl-biphenyl-4-yl]-1-ethyl-propyl}-2-methyl-phenoxymethyl)-dihydro-furan-2-one

HRID 546833Notes

Reaction equation

HRID 546833 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:9]=[C:10]([CH:14]([O:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:15]([CH3:18])([CH3:17])[CH3:16])[CH:11]=[CH:12][CH:13]=1.[CH2:24]([C:26]([C:45]1[CH:58]=[CH:57][C:48]([O:49][CH2:50][C@@H:51]2[O:55][C:54](=[O:56])[CH2:53][CH2:52]2)=[C:47]([CH3:59])[CH:46]=1)([C:29]1[CH:34]=[CH:33][C:32](B2OC(C)(C)C(C)(C)O2)=[C:31]([CH3:44])[CH:30]=1)[CH2:27][CH3:28])[CH3:25].C(OCC)(=O)C>CN(C)C=O>[CH3:16][C:15]([CH3:18])([CH3:17])[CH:14]([C:10]1[CH:9]=[C:8]([C:32]2[CH:33]=[CH:34][C:29]([C:26]([C:45]3[CH:58]=[CH:57][C:48]([O:49][CH2:50][C@@H:51]4[O:55][C:54](=[O:56])[CH2:53][CH2:52]4)=[C:47]([CH3:59])[CH:46]=3)([CH2:24][CH3:25])[CH2:27][CH3:28])=[CH:30][C:31]=2[CH3:44])[CH:13]=[CH:12][CH:11]=1)[O:19][Si:20]([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 57708911HCID 57708911, compoundHCID 57709209[1-(3-Bromo-phenyl)-2,2-dimethyl-propoxy]-trimethyl-silane

Product 1

HCID 577091665(R)-(4-{1-[3'-(2,2-dimethyl-1-trimethylsilanyloxy-propyl)-2-methyl-biphenyl-4-yl]-1-ethyl-propyl}-2-methyl-phenoxymethyl)-dihydro-furan-2-oneYield 28.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A [1,1′-bis(diphenylphosphino)ferrocene]palladium dichloride dichloromethane complex (1.68 mg, 0.002 mmol), a 2 M sodium carbonate aqueous solution (0.1 mL, 0.2 mmol) and [1-(3-bromo-phenyl)-2,2-dimethyl-propoxy]-trimethyl-silane (Example 18-(1); 43.16 mg, 0.137 mmol) were added to a solution of (R)-5-(4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenoxymethyl)-dihydro-furan-2-one (Example 15-(3); 33.7 mg, 0.068 mmol) in N,N-dimethylformamide (0.1 mL) at room temperature, and the mixture was stirred at 85° C. for 13.5 hours. Ethyl acetate was added to the reaction solution. The organic layer was washed with distilled water and brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/ethyl acetate=3/1) to give the title compound (11.7 mg, 28.5%).

Workup

  1. washThe organic layer was washed with distilled water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel chromatography (n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-72e5ebaeadd1438e8bf1ad524864afc3
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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