p-Toluenesulfonic acid → 2H-Pyran, tetrahydro-2-(2-iodoethoxy)-

Freshly distilled dihydropyran (Aldrich, 59.0 g, 0.7 mol) was added dropwise to a cooled solution of 2-iodoethanol (Aldrich, 98 g, 0.57 mol) in Et2O (1L) containing 0.1 g of p-toluenesulfonic acid (Eastman). The solution was then stirred for 1 h at 5°. Solid K2CO3Mallinckrodt, 5 g) was then added to the reaction mixture and the resulting suspension stirred an additional 1 h at RT. The reaction was then filtered and the remaining solid washed with Et2O (1 L). The organic solutions were combined and concentrated rotary evaporation (in a flask washed with 1% NEt3 in H2O). The crude 2-(2-iodoethoxy)-tetrahydro-2-H-pyran (~100 g, 68.9%) was used without further purification.

1. additionSolid K2CO3Mallinckrodt, 5 g) was then added to the reaction mixture
2. stirringthe resulting suspension stirred an additional 1 h at RT
3. filtrationThe reaction was then filtered
4. washthe remaining solid washed with Et2O (1 L)
5. concentrationconcentrated rotary
6. customevaporation (in a flask washed with 1% NEt3 in H2O)
7. customThe crude 2-(2-iodoethoxy)-tetrahydro-2-H-pyran (~100 g, 68.9%) was used without further purification

ORD record

ord-3b9c1663b5864425807018de9e484861

Source dataset

uspto-grants-1989_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04808632