Water → 2-Methyl-5-(trimethylsilyl)phenol

HRID 2217095

Reaction equation

HRID 2217095 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][C:10]([Si:13]([CH3:16])([CH3:15])[CH3:14])=[CH:9][C:3]=1[O:4][Si](C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C(OCC)C>[CH3:14][Si:13]([CH3:15])([CH3:16])[C:10]1[CH:11]=[CH:12][C:2]([CH3:1])=[C:3]([OH:4])[CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 59824830Trimethyl{4-methyl-3-[(trimethylsilyl)oxy]phenyl}silane2×

Product 1

HCID 597674632-Methyl-5-(trimethylsilyl)phenolYield 56%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2-methyl-5-(trimethylsilyl)phenoxytrimethylsilane (Intermediate 2; 5 g) in diethyl ether (40 mL) at room temperature was added tetrabutylammonium fluoride (TBAF; 19.3 mL, 1.0 M solution, 19.3 mmol). The reaction was stirred at this temperature for 5 minutes and then water (40 mL) was added. The mixture was extracted with diethyl ether (2×40 mL) and the combined organic extracts were dried (magnesium sulphate), concentrated under reduced pressure and purified by column chromatography (SiO2; light petroleum to 9:1 light petroleum-diethyl ether) to give the title compound as a colourless oil (1.9 g, 56%). Rf=0.32 (9:1 light petroleum-diethyl ether). 1H NMR δH 0.26 (9 H, s), 2.27 (3 H, s), 4.62 (1 H, s), 6.93 (1 H, d, J=1.0 Hz), 7.02 (1 H, dd, J=7.3, 1.0 Hz), 7.15 (1 H, d, J=7.3 Hz).

Workup

  1. extractionThe mixture was extracted with diethyl ether (2×40 mL)
  2. dry with materialthe combined organic extracts were dried (magnesium sulphate)
  3. concentrationconcentrated under reduced pressure
  4. custompurified by column chromatography (SiO2; light petroleum to 9:1 light petroleum-diethyl ether)

Sources & evidence

ORD record
ord-509c6fc12d4b478bab3a8dff8a20337b
Source dataset
uspto-grants-2008_08
Patent number
US07407649B2

Linked notes

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