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

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:18]([O-:20])=[O:19])=[C:6]([CH:17]=1)[O:7][C@@H:8]1[CH2:12][O:11][C@@H:10]2[C:13](=[O:16])[CH2:14][O:15][C@H:9]12.[C:21](#N)[CH3:22].[CH2:24]([SiH](CC)CC)C>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:18]([O-:20])=[O:19])=[C:6]([CH:17]=1)[O:7][C@@H:8]1[CH2:12][O:11][C@@H:10]2[C@H:13]([O:16][CH:21]([CH3:22])[CH3:24])[CH2:14][O:15][C@H:9]12

Participants

Reactant 3

HCID 6342Acetonitrile

HCID 12052Triethylsilane

HCID 86718460(3R,3aR,6aS)-3-(5-fluoro-2-nitro-phenoxy)-2,3,3a,6a-tetrahydrofuro[3,2-b]furan-6-one

Product 1

HCID 86718461(3R,3aR,6R,6aR)-3-(5-fluoro-2-nitro-phenoxy)-6-isopropoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan

Procedure

To 0.9 g (3.2 mmol) (3R,3aR,6aS)-3-(5-fluoro-2-nitro-phenoxy)-2,3,3a,6a-tetrahydrofuro[3,2-b]furan-6-one (III.7) and 0.1 g (0.32 mmol) FeCl3 in acetonitrile 1.3 g (9.7 mmol) isopropoxytrimethylsilane and 1.3 g (9.7 mmol) triethylsilane are added and the reaction mixture is stirred at RT for 5 h. Additional FeCl3 is added and the reaction mixture are stirred over night. The reaction mixture is quenched by addition of pH 7 buffer solution and extracted with EtOAc. The organic phases are pooled, dried and evaporated. The residue is purified by FC.