Reaktion #480871

Reaktionsgleichung

water

Lithium diisopropylamide

tetrahydropyran-4-carboxylic acid methyl ester

diiodomethane

→

title compound

Ausbeute 53.0%

4-Iodomethyltetrahydropyran-4-carboxylic acid methyl ester

Ausbeute 53.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITwas continued for a further hour during which it
2. 2
   Extraktionextracted with diethyl ether (3×40 ml)
3. 3
   WaschenThe combined organics were washed with water (2×20 ml), 2 M hydrochloric acid (20 ml), water (20 ml) and brine (20 ml)
4. 4
   TrocknenAfter drying (MgSO4)
5. 5
   Filtrationfiltering
6. 6
   Sonstigeevaporating under reduced pressure a yellow oil
7. 7
   Sonstigewas obtained which
8. 8
   Sonstigewas purified by column chromatography
9. 9
   Wascheneluting with 3.1 hexane/diethyl ether

Vorschrift

Lithium diisopropylamide (10.9 ml of 2.0M solution in heptane/tetrahydrofuran/ethylbenzene) was added to a stirred solution of tetrahydropyran-4-carboxylic acid methyl ester (3.00 g) in tetrahydrofuran (50 ml) at 0° C. under an atmosphere of nitrogen. The mixture was stirred for 30 minutes before dropwise addition of diiodomethane (2.51 ml). Stirring was continued for a further hour during which it warmed to room temperature. The reaction was poured into water (50 ml) and then extracted with diethyl ether (3×40 ml). The combined organics were washed with water (2×20 ml), 2 M hydrochloric acid (20 ml), water (20 ml) and brine (20 ml). After drying (MgSO4), filtering and evaporating under reduced pressure a yellow oil was obtained which was purified by column chromatography eluting with 3.1 hexane/diethyl ether to give the title compound as a colourless oil (3.11 g, 53%).

Quelle