Tetrabutylammonium Fluoride → tert-Butyl(5-ethyl-2-fluorophenoxy)dimethylsilane

HRID 2105050Notes

Reaction equation

HRID 2105050 reaction equation
[Si:1]([O:8][C:9]1[C:10]([F:19])=[C:11]([CH:14]=[C:15]([CH2:17][CH3:18])[CH:16]=1)C=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOC(C)=O>[C:4]([Si:1]([O:8][C:9]1[CH:16]=[C:15]([CH2:17][CH3:18])[CH:14]=[CH:11][C:10]=1[F:19])([CH3:3])[CH3:2])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 598380723-{[tert-Butyl(dimethyl)silyl]oxy}-5-ethyl-2-fluorobenzaldehyde

Product 1

HCID 59838026tert-Butyl(5-ethyl-2-fluorophenoxy)dimethylsilaneYield 254.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Intermediate 368.2 (394 mg, 0.50 mmol) and 1 M TBAF (in THF) in THF (10 mL) was stirred for 2 h. The mixture was dilute with EtOAc and washed with H2O (3×50 mL) and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 60% EtOAc/hexanes gradient) to afford 324 mg of Intermediate 368.1. LCMS (2 min gradient) RT=2.06 min, 669.5 (M+H)+.

Workup

  1. washwashed with H2O (3×50 mL) and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography (0 to 60% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-259997355d154cbfae58816c6b929997
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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