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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1396643Generated: October 30, 2026

Water → (3R,3aR,6R,6aR)-3-ethoxy-6-(5-fluoro-2-nitro-phenoxy)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan

https://huagongshe.com/reaction/1396643

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantIodoethaneHCID 6340—
ReactantSodium hydrideHCID 24758—
Reactant(3R,3aR,6R,6aR)-6-(5-fluoro-2-nitro-phenoxy)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-olHCID 86718453—
SolventDimethylformamideHCID 6228—
SolventEthyl AcetateHCID 8857—
Product(3R,3aR,6R,6aR)-3-ethoxy-6-(5-fluoro-2-nitro-phenoxy)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furanHCID 86718463—

Reaction Steps

To 1.1 g (3.8 mmol) (3R,3aR,6R,6aR)-6-(5-fluoro-2-nitro-phenoxy)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol (III.1), 0.88 g (5.6 mmol) ethyl iodide in DMF, 0.2 g (4.1 mmol) NaH (55% in mineral oil) are added and the temperature is kept below 35° C. The mixture is stirred at RT for 1 h. Water and EtOAc are added and the organic layer is separated, washed with water, dried and evaporated. The residue was purified by FC.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08901138B2
Source datasetuspto-grants-2014_12
ORD IDord-ab315cd7c72d4d29a800f052cb3c5dcd
Source noteuspto-grants-2014_12