tert-Butyldimethylsilyl chloride → HCID 19385687, compound

HRID 2399486Notes

Reaction equation

HRID 2399486 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].[C:13]([Si:17]([CH3:20])([CH3:19])Cl)([CH3:16])([CH3:15])[CH3:14]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Si:17]([O:12][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[Cl:1])([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:20])[CH3:19]

Participants

5

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 77580Methyl 3-chloro-4-hydroxybenzoate

Product 1

HCID 19385687HCID 19385687, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.00 g (26.8 mmol) of methyl 3-chloro-4-hydroxybenzoate dissolved in 40 mL of CH2Cl2 was added 6.55 g (53.6 mmol) of 4-dimethylaminopyridine, 4.85 g (32.2 mmol) of tert-butyldimethylchlorosilane and the mixture was stirred at room temperature for 3.5 hours. The reaction mixture was filtered, diluted with ethyl acetate, washed with 0.1N HCl, saturated NaHCO3, and brine. The product layer was then dried (MgSO4), filtered and evaporated in vacuo to afford 8.05 g (100%) of the title compound.

Workup

  1. filtrationThe reaction mixture was filtered
  2. additiondiluted with ethyl acetate
  3. washwashed with 0.1N HCl, saturated NaHCO3, and brine
  4. dry with materialThe product layer was then dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-f039a8f718c6490caeb744571025ea7d
Source dataset
uspto-grants-1995_09
Patent number
US05449682

Reaction notes

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