Reaktion #1763177

Reaktionsgleichung

1,4:3,6-dianhydro-D-mannitol

5-hexenoic acid

EDAC

→

title compound

(3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl hex-5-enoate

Lösungsmittel

DCM

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with a solution of NaHPO4 5% (2×40 mL) and brine
2. 2
   TrocknenThe organic layer was dried over sodium sulfate
3. 3
   Einengenconcentrated under vacuo
4. 4
   SonstigeThe residue was purified by flash chromatography (Biotage SP1, 40+M column, TLC method: n-Hexane/EtOAc −8:2, Rf product: 0.35)

Vorschrift

To a stirred solution of 1,4:3,6-dianhydro-D-mannitol (isommanide) (2.00 g, 13.68 mmol), 5-hexenoic acid (1.60 g, 13.68 mmol) and DMAP (0.17 g, 1.4 mmol) in DCM (50 mL) cooled at 0° C., EDAC (3.1 g, 16.42 mmol) was added. The solution was stirred at room temperature for 6 hrs. The solution was diluted with DCM (30 mL), washed with a solution of NaHPO4 5% (2×40 mL) and brine. The organic layer was dried over sodium sulfate and concentrated under vacuo. The residue was purified by flash chromatography (Biotage SP1, 40+M column, TLC method: n-Hexane/EtOAc −8:2, Rf product: 0.35) yielding the title compound.

Quelle