Trimethylsilyl triflate → Methyl 1,4-dioxaspiro[4.5]decane-7-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Trimethylsilyl triflate	HCID 65367	—
Reactant	2,2,7,7-Tetramethyl-3,6-dioxa-2,7-disilaoctane	HCID 81858	—
Reactant	Methyl 3-oxocyclohexane-1-carboxylate	HCID 566099	—
Solvent	Dichloromethane	HCID 6344	—
Product	Methyl 1,4-dioxaspiro[4.5]decane-7-carboxylate	HCID 372311	—

Reaction Conditions

Temperature	-78 °C

Reaction Steps

To a solution of trimethylsilyltrifluoromethanesulfonate (0.034 mL) in dry dichloromethane (5 mL) was added 1,2-bis(trimethylsiloxy)ethane (4.55 mL) followed by methyl 3-oxocyclohexanecarboxylate (2.9 g). The reaction mixture was stirred for 3 hours at −78° C. The reaction mixture was quenched with dry pyridine (0.5 mL), poured into saturated aqueous NaHCO3, and extracted with ether. The ether layer was dried over Na2CO3/Na2SO4. The reaction mixture was concentrated and purified by flash chromatography on silica with 5 to 30% ethyl acetate in hexanes to provide the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09174982B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-ccab818e9a8847958280b228c5ec5b04
Source note	uspto-grants-2015_11