Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1396642Generated: November 1, 2026

Ammonium Chloride → (3R,3aR,6R,6aS)-3-(5-fluoro-2-nitro-phenoxy)-6-methyl-3,3a,5,6a-tetrahydro-2H-furo[3,2-b]furan-6-ol

https://huagongshe.com/reaction/1396642

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAmmonium ChlorideHCID 25517—
Reactant(3R,3aR,6aS)-3-(5-fluoro-2-nitro-phenoxy)-2,3,3a,6a-tetrahydrofuro[3,2-b]furan-6-oneHCID 86718460—
ReactantHCID 178418348HCID 178418348—
SolventDiethyl EtherHCID 3283—
SolventTetrahydrofuranHCID 8028—
Product(3R,3aR,6R,6aS)-3-(5-fluoro-2-nitro-phenoxy)-6-methyl-3,3a,5,6a-tetrahydro-2H-furo[3,2-b]furan-6-olHCID 86718462—

Reaction Steps

1.6 g (5.7 mmol) (3R,3aR,6aS)-3-(5-fluoro-2-nitro-phenoxy)-2,3,3a,6a-tetrahydrofuro[3,2-b]furan-6-one (III.7) in THF are cooled to −70° C. 3.5 ml (5.7 mmol) 1.6 mol/l methyl lithium in diethyl ether are added dropwise and the reaction mixture is allowed to reach RT and stirred for 2.5 h. Aqueous NH4Cl solution and diethyl ether are added and the organic layer is separated, dried and evaporated. The residue is purified by FC (Al2O3).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08901138B2
Source datasetuspto-grants-2014_12
ORD IDord-2c027ff4423e42bfa9b70c25e5197919
Source noteuspto-grants-2014_12