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

HRID 619817Notes

Reaction equation

HRID 619817 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1.[CH2:9]1[CH2:19][CH2:18]N2C(=NCCC2)CC1.[CH3:20][SiH:21](Cl)[CH3:22].[CH2:24](Cl)Cl>CCOC(C)=O>[CH3:18][C:19]([Si:21]([CH3:22])([CH3:20])[O:1][C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1)([CH3:9])[CH3:24]

Participants

6

Reactant 4

HCID 342M-CresolHCID 6344DichloromethaneHCID 66108ChlorodimethylsilaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 529234tert-Butyl(dimethyl)(3-methylphenoxy)silane

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-hydroxytoluene (2 g, 8.5 mmol) in 20 mL of CH2Cl2 is added DBU (3.32 mL, 22.2 mmol) and 1,1-dimethylethyl)dimethylsilyl chloride (3.07 g, 20.34 mmol). After 1.5 hours, the solution is diluted with EtOAc. The organic solution is washed with 1 N HCl, 10% Na2CO3 and saturated NaCl. The organic layer is dried over MgSO4, filtered, and concentrated. The crude product is purified by column chromatography eluting with 5% EtOAc/hexanes to afford the title compound (4.1 g, 18.5 mmol) as an oil.

Workup

  1. washThe organic solution is washed with 1 N HCl, 10% Na2CO3 and saturated NaCl
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is purified by column chromatography
  6. washeluting with 5% EtOAc/hexanes

Sources & evidence

ORD record
ord-edd633f43b38437f9ffd28465b055f9a
Source dataset
uspto-grants-1999_09
Patent number
US05958918

Reaction notes

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