tert-Butyldimethylsilyl chloride → Methyl 2-(4-tert-butyldimethylsilyloxymethylphenoxy)acetate

HRID 2399500Notes

Reaction equation

HRID 2399500 reaction equation
[OH:1][CH2:2][C:3]1[CH:14]=[CH:13][C:6]([O:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1.[C:15]([Si:19]([CH3:22])([CH3:21])Cl)([CH3:18])([CH3:17])[CH3:16]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Si:19]([O:1][CH2:2][C:3]1[CH:14]=[CH:13][C:6]([O:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:22])[CH3:21]

Participants

5

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 690034Methyl 2-(4-hydroxymethylphenoxy)acetate

Product 1

HCID 19385670Methyl 2-(4-tert-butyldimethylsilyloxymethylphenoxy)acetateYield 99.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4.00 g (20.4 mmol) of the product of Step A dissolved in 30 mL of CH2Cl2 was added 5.00 g (40.8 mmol) of 4-dimethylaminopyridine and 3.69 g (24.5 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. Drying in vacuo afforded 6.30 g (99%) 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. customDrying in vacuo

Sources & evidence

ORD record
ord-b6bc6e7e408948b4962e9df87ddea598
Source dataset
uspto-grants-1995_09
Patent number
US05449682

Reaction notes

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