Chlorotrimethylsilane → HCID 68539762, compound

HRID 1992248Notes

Reaction equation

HRID 1992248 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[OH:9].C(N(CC)CC)C.[CH3:17][Si:18](Cl)([CH3:20])[CH3:19].C(OCC)(=O)C>ClCCl.O>[CH3:17][Si:18]([CH3:20])([CH3:19])[C:3]1([OH:9])[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][CH:2]1[CH3:1]

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 77712,4-DimethylphenolHCID 8471TriethylamineHCID 8857Ethyl Acetate

Product 1

HCID 68539762HCID 68539762, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2,4-dimethyl phenol (5.47 g, 44.8 mmol) in dry dichloromethane (120 ml) at 0° C. under nitrogen was added triethylamine (1.1 eq., 4.99 g, 6.9 ml) followed by the slow addition of trimethyl silyl chloride (1.05 eq., 5.11 g, 6.00 ml). The reaction was monitored by thin layer chromatography (10% ethyl acetate in 60-80 light petroleum) and upon completion (˜2 hr) water (50 ml) was added. The organic layer was washed with water (2×50 ml), dried (Na2SO4), filtered and the solvent removed to give the title compound (8.13 g, 93%).

Workup

  1. additionwas added
  2. washThe organic layer was washed with water (2×50 ml)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent removed

Sources & evidence

ORD record
ord-aa0ce0446f2641f3b74ce56ddf4a242d
Source dataset
uspto-grants-2010_01
Patent number
US07648966B2

Reaction notes

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