tert-Butanol → 2,2-DIMETHYLTETRAHYDRO-2H-PYRAN-4-CARBONITRILE

https://huagongshe.com/reaction/2088959

Participants

Role	Name	HCID	Charge
Reactant	tert-Butanol	HCID 6386	—
Reactant	Tosylmethyl isocyanide	HCID 161915	—
Reactant	2,2-Dimethyltetrahydropyran-4-one	HCID 1738159	—
Reactant	Potassium tert-butoxide	HCID 23665647	—
Solvent	Diethyl Ether	HCID 3283	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Product	2,2-DIMETHYLTETRAHYDRO-2H-PYRAN-4-CARBONITRILE	HCID 12296425	84.4%

Reaction Conditions

Temperature	-20 °C

Reaction Steps

p-Toluenesulfonylmethyl isocyanide (693 mg) and tert-butanol (438 μl) were added to a solution of 2,2-dimethyltetrahydro-4H-pyran-4-one (350 mg) in dimethoxyethane (10 ml) with stirring. Potassium tert-butoxide (766 mg) were added in three portions under cooling at −20° C. The mixture was heated to room temperature and then stirred for 18 hours. Diethyl ether was added and the mixture was filtered through Celite. Thereafter, the solvent was evaporated under reduced pressure to give the title compound (321 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08436012B2
Source dataset	uspto-grants-2013_05
ORD ID	ord-275f141250b7490c9e50328f6eb7b12b
Source note	uspto-grants-2013_05