Water → HCID 59517034, compound

HRID 1161380Notes

Reaction equation

HRID 1161380 reaction equation
[CH3:1][CH2:2][CH2:3]C[N+](CCCC)(CCCC)CCCC.[F-].[OH2:19].[C:20]([O:23][CH2:24][CH3:25])(=O)C.[CH2:26]1[CH2:30][O:29][CH2:28][CH2:27]1>>[CH3:20][O:23][C:24]1[CH:25]=[C:2]([CH2:3][OH:19])[CH:1]=[C:26]([CH2:30][O:29][CH3:28])[CH:27]=1

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 59517034HCID 59517034, compound

Procedure

To a solution of the residue in 10 ml of THF there was added 4.3 ml of TBAF (1.0 M, THF solution) at 0° C., and the mixture was stirred at room temperature for 17 hours and 30 minutes. Water was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (618 mg) as a light yellow oil.

Workup

  1. washThe organic layer was washed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationThe desiccating agent was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Sources & evidence

ORD record
ord-0c7053c68db644cbaa3173fefda06f3e
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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