Tetrabutylammonium Fluoride → 2-Hydroxy-4'(methylthio)isobutyrophenone

HRID 357228Notes

Reaction equation

HRID 357228 reaction equation
C[Si](C)(C)[O:3][C:4]([CH3:16])([CH3:15])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=1)=[O:6].[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:3][C:4]([CH3:16])([CH3:15])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=1)=[O:6]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 184001902-Trimethylsilyloxy-4'-(methylthio)isobutyrophenone

Product 1

HCID 114131682-Hydroxy-4'(methylthio)isobutyrophenoneYield 84.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 40 mg (0.14 mmol) of 2-trimethylsilyloxy-4'-(methylthio)isobutyrophenone in 2 mL THF was added 0.2 mL of 1M n-Bu4NF in THF. The resulting mixture was stirred for 30 min and then quenched with 10 mL of NH4OAc buffer. The product was extracted with EtOAc, dried over MgSO4 and concentrated. The residue was purified by flash chromatography, eluting with 4:1 hexane/EtOAc to give 25 mg of the title product.

Workup

  1. customquenched with 10 mL of NH4OAc buffer
  2. extractionThe product was extracted with EtOAc
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. washeluting with 4:1 hexane/EtOAc

Sources & evidence

ORD record
ord-a3ddf91807b94059a2eb3fc0708620b9
Source dataset
uspto-grants-1998_11
Patent number
US05840746

Reaction notes

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