2-Butene-1,4-diol → (Z)-4-(Tetrahydro-2H-pyran-2-yl-oxy)but-2-en-1-ol

Participants

Role	Name	HCID	Charge
Reactant	2-Butene-1,4-diol	HCID 8065	—
Reactant	3,4-dihydro-2H-pyran	HCID 8080	—
Reactant	Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)	HCID 466102	—
Solvent	Tetrahydrofurane dichloromethane	HCID 21919333	—
Product	(Z)-4-(Tetrahydro-2H-pyran-2-yl-oxy)but-2-en-1-ol	HCID 10975949	481.9%

Reaction Conditions

Temperature	0 °C

Reaction Steps

Dihydropyrane (9.1 ml, 100 mmol) was added dropwise to a cooled (0° C.) solution of 2-butene-1,4-diol (8.8 g, 10 mmol) and pyridinium paratoluenesulfonate (0.25 g, 10 mmol) in anhydrous dichloromethane:tetrahydrofuran (2:1). The mixture was stirred two days at 0° C. then concentrated in vacuo. The residue was purified by flash chromatography on silica gel (ethyl acetate:hexane 3:7) to give 8.3 g of the title compound (49%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05308837
Source dataset	uspto-grants-1994_05
ORD ID	ord-87867444b2bc4c5b9fe2dd7ddd3d0478
Source note	uspto-grants-1994_05