Diiodomethane → 4-Iodomethyl-tetrahydro-pyran-4-carboxylic acid methyl ester

To a stirred solution of methyl tetrahydropyran-4-carboxylate (3.00 g) in anhydrous THF (50 ml) under nitrogen at 0° C. was added a solution of lithium di-isopropylamide (2.0 M, 10.9 ml). After 30 minutes, diiodomethane (8.36 g) was added and the mixture was allowed to warm up to RT and then stirred for 1 h. The mixture was poured onto water (50 ml) and extracted with ether (3×40 ml). The combined ether layers were washed with water (2×20 ml), aqueous hydrochloric acid (2 M, 20 ml), water (20 ml) and brine (20 ml), dried (MgSO4) and evaporated under reduced pressure. The residue was purified on silica gel, eluting with 3:1 hexane/ether, to give the title compound (3.11 g) as a colourless oil.

1. additionThe mixture was poured onto water (50 ml)
2. extractionextracted with ether (3×40 ml)
3. washThe combined ether layers were washed with water (2×20 ml), aqueous hydrochloric acid (2 M, 20 ml), water (20 ml) and brine (20 ml)
4. dry with materialdried (MgSO4)
5. customevaporated under reduced pressure
6. customThe residue was purified on silica gel
7. washeluting with 3:1 hexane/ether

ORD record

ord-be97c69ba959461fa07af2f3afd8450e

Source dataset

uspto-grants-2004_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06680338B2