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

HRID 546830Notes

Reaction equation

HRID 546830 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:9]=[C:10]([C:14]([CH2:22][CH3:23])([O:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH2:15][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>[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]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([CH2:22][CH3:23])([O:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH2:15][CH3:16])[CH:9]=2)=[C:31]([CH3:44])[CH:30]=1)[CH2:27][CH3:28])[CH3:25]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 57708911(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-oneHCID 57709150HCID 57709150, compound

Product 1

HCID 57709099(R)-5-(4-{1-ethyl-1-[3'-(1-ethyl-1-trimethylsilanyloxy-propyl)-2-methyl-biphenyl-4-yl]-propyl}-2-methyl-phenoxymethyl)-dihydro-furan-2-oneYield 49.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A [1,1′-bis(diphenylphosphino)ferrocene]palladium dichloride dichloromethane complex (1.49 mg, 0.002 mmol), a 2 M sodium carbonate solution (0.1 mL, 0.2 mmol) and [1-(3-bromo-phenyl)-1-ethyl-propoxy]-trimethyl-silane (Example 17-(1); 26.25 mg, 0.091 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); 30 mg, 0.061 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, developed twice) to give the title compound (18 mg, 49.2%).

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-f00003db933f489a890156e8905ea60c
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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