tert-Butyldimethylsilyl chloride → HCID 19385657, compound

HRID 2399492Notes

Reaction equation

HRID 2399492 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:13])[C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].[C:14]([Si:18]([CH3:21])([CH3:20])Cl)([CH3:17])([CH3:16])[CH3:15]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Si:18]([O:12][C:11]1[C:2]([Cl:1])=[CH:3][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:9][C:10]=1[Cl:13])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:21])[CH3:20]

Participants

5

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 76856Methyl 3,5-dichloro-4-hydroxybenzoate

Product 1

HCID 19385657HCID 19385657, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 10.00 g (45.2 mmol) of methyl 3,5-dichloro-4-hydroxybenzoate dissolved in 100 mL of CH2Cl2 was added 11.06 g (90.2 mmol) of 4-dimethylaminopyridine and 8.18 g (54.2 mmol) of tert-butyldimethylchlorosilane and the mixture was stirred under N2 for 5 hours. The reaction mixture was then filtered and the filtrate was diluted with ethyl acetate. The solution was washed with water, 1N HCl, saturated NaHCO3, dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 5% ethyl acetate/hexane to afford 7.70 g (51%) of the title compound.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. additionthe filtrate was diluted with ethyl acetate
  3. washThe solution was washed with water, 1N HCl, saturated NaHCO3
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified on a silica gel flash chromatography column
  8. washeluted with 5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-6d2c369886ec465c9134c8173a2b11c3
Source dataset
uspto-grants-1995_09
Patent number
US05449682

Reaction notes

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