tert-Butyldimethylsilyl chloride → Ethyl 2-((tert-butyldimethylsilyl)oxy)-6-methylbenzoate

HRID 2188014Notes

Reaction equation

HRID 2188014 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:6]=1[OH:12])[CH3:2].[C:14]([Si:18](Cl)([CH3:20])[CH3:19])([CH3:17])([CH3:16])[CH3:15].C(N(C(C)C)CC)(C)C>ClCCl>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:6]=1[O:12][Si:18]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:20])[CH3:19])[CH3:2]

Participants

5

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 584222Ethyl 2-hydroxy-6-methylbenzoate

Product 1

HCID 69585527Ethyl 2-((tert-butyldimethylsilyl)oxy)-6-methylbenzoateYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-hydroxy-6-methyl-benzoic acid ethyl ester (5.00 g, 27.8 mmol) and t-butyl-di-methylsilyl chloride (6.27 g, 41.6 mmol) in dichloromethane (100 ml) was added diisopropyl ethylamine. The solution was stirred at 50° C. for 24 hours, washed with water, brine, dried (MgSO4), filtered and the solvent evaporated in vacuo, which afforded 7.6 g (93%) of 2-(tert-butyl-dimethyl-silanyloxy)-6-methyl-benzoic acid ethyl ester as an oil.

Workup

  1. washwashed with water, brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent evaporated in vacuo, which

Sources & evidence

ORD record
ord-446bf611177844abb603d7372db184a5
Source dataset
uspto-grants-2002_06
Patent number
US06410556B1

Reaction notes

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