Tetrabutylammonium Fluoride → HCID 59541930, compound

HRID 1893264Notes

Reaction equation

HRID 1893264 reaction equation
C([Si](C)(C)[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH:14]=2)=[CH:9][CH:8]=1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH:14]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59541984HCID 59541984, compound

Product 1

HCID 59541930HCID 59541930, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-cyclohex-3-enone (2.0 g, 6.62 mmol) in THF was treated with TBAF (1N in THF, 10 mL, 9.93 mmol) at room temperature. After 10 min., the solvent was removed and the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered, and the filtrate concentrated in vacuo to give colorless oil, which was purified on a silica gel column by a CombiFlash® system using hexanes and ethyl acetate as eluent (from pure hexanes to pure ethyl acetate) to afford the title compound as a white solid.

Workup

  1. customthe solvent was removed
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customto give colorless oil, which
  8. customwas purified on a silica gel column by a CombiFlash® system

Sources & evidence

ORD record
ord-b191e22fb0994b2fb84741ec919c8a39
Source dataset
uspto-grants-2013_08
Patent number
US08513229B2

Reaction notes

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