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

HRID 1019186Notes

Reaction equation

HRID 1019186 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 8028TetrahydrofuranSolvent

Procedure

To a solution of 40 mg (0.14 mmol) of 2-trimethylsilyloxy-4′-(methylthio)isobutyrophenone in 2 niL TEF was added 0.2 mL of 1 M 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 tide product. 1H NMR (CD3COCD3) d 1.50 (6H, s), 2.54 (3H, s), 4.68 (1H, s), 7.30 (2H, d), 8.15 (2H, d).

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-077da6f28c5543ad84a9f7977798c5b1
Source dataset
uspto-grants-2002_11
Patent number
US06486194B2

Reaction notes

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