M-Cresol → tert-Butyl(dimethyl)(3-methylphenoxy)silane

HRID 1710880Notes

Reaction equation

HRID 1710880 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:8].[Si:9](Cl)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]>C(Cl)Cl>[C:12]([Si:9]([CH3:11])([CH3:10])[O:7][C:6]1[CH:1]=[C:2]([CH3:8])[CH:3]=[CH:4][CH:5]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 342M-CresolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 529234tert-Butyl(dimethyl)(3-methylphenoxy)silaneYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of m-cresol(1 mL, 9.6 mmol) in CH2Cl2 (10 mL) was added tert-butyldimethylsilyl chloride (1.5 g, 10 mmol), triethyl aimine (3 ml, 20 mmol. The reaction was stirred at room temperature overnight. It was filtered and filtrate was concentrated and purified by column chromatography on ISCO (40 g) with 10% ethyl acetate in hexanes to yield tert-butyldimethyl(m-tolyloxy)silane as a colorless oil (1.31 g, 62%). HPLC retention time (Method C)=3.22 min. LC/MS (ESD (M+H)+=223.

Workup

  1. filtrationIt was filtered
  2. concentrationfiltrate was concentrated
  3. custompurified by column chromatography on ISCO (40 g) with 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-91c45f077f6849988602ea4697fc1d74
Source dataset
uspto-grants-2010_09
Patent number
US07790745B2

Reaction notes

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