Tetrabutylammonium Fluoride → HCID 10836187, compound

HRID 1198764Notes

Reaction equation

HRID 1198764 reaction equation
[C:1]([O:4][CH:5]([C:7]1[C:8]([CH2:31][O:32][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:9][C:10]2[C:15]([C:16]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH:14][CH:13]=[C:12]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:11]=2)[CH3:6])(=[O:3])[CH3:2].[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:1]([O:4][CH:5]([C:7]1[C:8]([CH2:31][OH:32])=[CH:9][C:10]2[C:15]([C:16]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH:14][CH:13]=[C:12]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:11]=2)[CH3:6])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 10842123HCID 10842123, compound

Product 1

HCID 10836187HCID 10836187, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the crude ether from Step 5 in THF (10 mL) at 0° C. was added HOAC (4 drops) followed by n-Bu4NF (1M, THF, 1.4 mL). The reaction mixture was stirred 2 hr. at 0° C. then quenched with a saturated solution of NH4Cl and diluted with Et2O. The organic phase was washed with H2O, brine, dried over MgSO4, and the solvent evaporated. The residue was purified by chromatography on silica gel using hexane/EtOAc, 7:3, to give the title product.

Workup

  1. customat 0° C. then quenched with a saturated solution of NH4Cl
  2. additiondiluted with Et2O
  3. washThe organic phase was washed with H2O, brine
  4. dry with materialdried over MgSO4
  5. customthe solvent evaporated
  6. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-93f5d5c022434f62a344ad92d24dc816
Source dataset
uspto-grants-1994_01
Patent number
US05281720

Reaction notes

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