Tetrabutylammonium Fluoride → HCID 57411302, compound

HRID 2278320Notes

Reaction equation

HRID 2278320 reaction equation
CC([Si](C(C)C)(C(C)C)[O:5][C:6]1[C:11]2[C:12]([CH3:16])([CH3:15])[CH2:13][O:14][C:10]=2[C:9]([CH3:17])=[CH:8][CH:7]=1)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:15][C:12]1([CH3:16])[C:11]2=[C:6]([OH:5])[CH:7]=[CH:8][C:9]([CH3:17])=[C:10]2[O:14][CH2:13]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67958584HCID 67958584, compound2×

Product 1

HCID 57411302HCID 57411302, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tris(1-methylethyl)[(3,3,7-trimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]silane (Intermediate 26, 3.6 g, 10.84 mmol) was dissolved in THF (36 mL) to obtain a dark yellow solution. TBAF (8.5 g, 32.5 mmol) was added and the reaction mixture was stirred overnight at room temperature. The solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate and washed with aqueous HCl, then aqueous NaHCO3 and finally brine. The organic solution was dried over Na2SO4 and evaporated to dryness and the residue was purified by flash chromatography on silica gel using cyclohexane to cyclohexane/ethyl acetate 95:5 as eluents affording the title compound (1.69 g) as colorless oil.

Workup

  1. customto obtain a dark yellow solution
  2. customThe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with aqueous HCl
  5. dry with materialThe organic solution was dried over Na2SO4
  6. customevaporated to dryness
  7. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-2268e360c89249aebc8b94eb0c3032e6
Source dataset
uspto-grants-2015_09
Patent number
US09133175B2

Reaction notes

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