Triethylamine → Methyl alpha-(4-tert-butyldimethylsilyloxymethyl-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetate

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Ethyl Acetate	HCID 8857	—
Reactant	tert-Butyldimethylsilyl chloride	HCID 28928	—
Reactant	N-(4-iso-propylbenzenesulfonyl)-alpha-(2-n-propyl-4-hydroxymethylphenoxy)-3,4-methylenedioxyphenylacetamide	HCID 19080378	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Solvent	Dichloromethane	HCID 6344	—
Product	Methyl alpha-(4-tert-butyldimethylsilyloxymethyl-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetate	HCID 22912473	97%

Reaction Steps

To a solution of 2.50 g (6.98 mmol) of the product of Step A dissolved in 20 mL of dichloromethane was added 1.95 mL (14.0 mmol) of triethylamine, 1.26 g (8.38 mmol) of tert-butyldimethylchlorosilane, 85 mg (0.1 eq) of 4-dimethylaminopyridine and the reaction mixture was stirred at room temperature for 30 minutes under a nitrogen atmosphere. The reaction was then diluted with 100 mL EtOAc, washed with water, 1.0N HCl, saturated aqueous NaHCO3, saturated NaCl, dried (MgSO4), filtered and evaporated in vacuo to afford 3.20 g (97%) of the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05668176
Source dataset	uspto-grants-1997_09
ORD ID	ord-aee381b695d74a1eac46e8f3ceb1a07a
Source note	uspto-grants-1997_09