Tetrabutylammonium Fluoride → HCID 66762192, compound

HRID 561859Notes

Reaction equation

HRID 561859 reaction equation
[Si]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:27]=[CH:26][C:15]([CH2:16][CH:17]([CH2:23][CH:24]=[CH2:25])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:14][CH:13]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:8][CH2:9][CH2:10][O:11][C:12]1[CH:27]=[CH:26][C:15]([CH2:16][CH:17]([CH2:23][CH:24]=[CH2:25])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66760696HCID 66760696, compound

Product 1

HCID 66762192HCID 66762192, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-[4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethoxy)benzyl]pent-4-enoate from the previous step (1 eq.) in THF (0.2 M) was added tetrabutylammonium fluoride (1.0 M THF solution, 2 eq.). The resulting reaction mixture was stirred at RT for 2 h. After quenching the reaction with sat. aq. NH4Cl, the mixture was extracted with ether. The combined organic extracts were washed with water and brine, dried over MgSO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 10:1 (v/v) Hex:EtOAc→EtOAc) afforded the title compound as a colorless oil.

Workup

  1. customThe resulting reaction mixture
  2. customAfter quenching
  3. customthe reaction with sat. aq. NH4Cl
  4. extractionthe mixture was extracted with ether
  5. washThe combined organic extracts were washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated in vacuo
  9. customPurification of the crude product
  10. customthus obtained by way of flash chromatography (SiO2, 10:1 (v/v) Hex:EtOAc→EtOAc)

Sources & evidence

ORD record
ord-a710b9526dc142a59f1fbfa8b5752ed5
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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