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

HRID 1396641Notes

Reaction equation

HRID 1396641 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

4

Reactant 3

HCID 6342AcetonitrileHCID 12052TriethylsilaneHCID 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.

Workup

  1. stirringthe reaction mixture are stirred over night
  2. customThe reaction mixture is quenched by addition of pH 7 buffer solution
  3. extractionextracted with EtOAc
  4. customdried
  5. customevaporated
  6. customThe residue is purified by FC

Sources & evidence

ORD record
ord-08802be16e6c45cb9c665837c49ab804
Source dataset
uspto-grants-2014_12
Patent number
US08901138B2

Reaction notes

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