Tetrabutylammonium Fluoride → HCID 58168497, compound

HRID 1255272Notes

Reaction equation

HRID 1255272 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[C:19]([O:22][CH2:23][CH2:24][C:25]1[S:26][CH:27]=[C:28]([CH2:30][CH2:31][O:32][Si](C(C)(C)C)(C)C)[CH:29]=1)(=[O:21])[CH3:20]>C1COCC1>[C:19]([O:22][CH2:23][CH2:24][C:25]1[S:26][CH:27]=[C:28]([CH2:30][CH2:31][OH:32])[CH:29]=1)(=[O:21])[CH3:20]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58168596HCID 58168596, compound

Product 1

HCID 58168497HCID 58168497, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (1M in THF, 3.65 mL) was added dropwise to a solution of 2-(4-(2-(tert-butyldimethylsilyloxy)ethyl)thiophen-2-yl)ethyl acetate [Aromatic Intermediate 21, step a] (1.2 g) in dry THF (30 mL). This solution was allowed to stand at 20° C. for 1 hour, then the solvents were evaporated under reduced pressure and the residue was purified by flash silica chromatography, using 40% ethyl acetate in isohexane as solvent. Fractions containing the product were evaporated to dryness to afford the subtitled compound. Yield 0.63 g.

Workup

  1. customthe solvents were evaporated under reduced pressure
  2. customthe residue was purified by flash silica chromatography
  3. additionFractions containing the product
  4. customwere evaporated to dryness

Sources & evidence

ORD record
ord-9b695a9a9bb0408f9e1843bffbd90f70
Source dataset
uspto-grants-2013_06
Patent number
US08455483B2

Reaction notes

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