Potassium Hydroxide → HCID 57443478, compound

HRID 546817Notes

Reaction equation

HRID 546817 reaction equation
[OH-].[K+].C([O:5][C:6](=[O:48])/[CH:7]=[CH:8]/[C:9]1[O:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([C:25]3[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][CH:33]([O:38][Si](C(C)(C)C)(C)C)[C:34]([CH3:37])([CH3:36])[CH3:35])=[C:27]([CH3:46])[CH:26]=3)([CH2:23][CH3:24])[CH2:21][CH3:22])=[CH:16][C:15]=2[CH3:47])=[CH:12][CH:13]=1)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.S(=O)(=O)(O)[O-].[K+]>CO.O1CCCC1.C(OCC)(=O)C>[CH2:21]([C:20]([C:17]1[CH:18]=[CH:19][C:14]([C:11]2[O:10][C:9](/[CH:8]=[CH:7]/[C:6]([OH:48])=[O:5])=[CH:13][CH:12]=2)=[C:15]([CH3:47])[CH:16]=1)([C:25]1[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][CH:33]([OH:38])[C:34]([CH3:36])([CH3:37])[CH3:35])=[C:27]([CH3:46])[CH:26]=1)[CH2:23][CH3:24])[CH3:22]

Participants

8

Reactant 4

HCID 14797Potassium HydroxideHCID 516920Potassium bisulfateHCID 2724141Tetrabutylammonium FluorideHCID 57708944HCID 57708944, compound

Product 1

HCID 57443478HCID 57443478, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A 1 N potassium hydroxide aqueous solution (2 mL) was added to a solution of (E)-3-{5-[4-(1-{4-[3-(t-butyl-dimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-2-methyl-phenyl]-furan-2-yl}-acrylic acid ethyl ester (Example 5-(1); 42 mg, 0.065 mmol) in methanol (2 mL) and tetrahydrofuran (2 mL) at room temperature, and the mixture was stirred at 60° C. for two hours. The reaction mixture was concentrated under reduced pressure, and ethyl acetate and a saturated aqueous potassium bisulfate solution were added to the residue. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (0.2 mL). A 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran (2 mL, 2 mmol) was added at room temperature, and the mixture was stirred at 65° C. for one hour. A potassium bisulfate aqueous solution and ethyl acetate were added to the reaction mixture to separate the layers. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by preparative TLC (hexane/ethyl acetate=1/2) to give the title compound (21.2 mg, 65%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and ethyl acetate
  2. additiona saturated aqueous potassium bisulfate solution were added to the residue
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in tetrahydrofuran (0.2 mL)
  7. stirringthe mixture was stirred at 65° C. for one hour
  8. customto separate the layers
  9. washThe organic layer was washed with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by preparative TLC (hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-ef4839ecdde948fd93b09896d70db666
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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