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

HRID 1396636Notes

Reaction equation

HRID 1396636 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[C@H:12]2[O:13][CH2:14][C@@H:15]([OH:16])[C@H:11]2[O:10][CH2:9]1.[OH-].[Na+].[CH2:23](Cl)Cl.S(OC)(OC)(=O)=O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[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[C@H:12]2[O:13][CH2:14][C@@H:15]([O:16][CH3:23])[C@H:11]2[O:10][CH2:9]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6497Dimethyl SulfateHCID 14798Sodium Hydroxide2×HCID 86718453(3R,3aR,6R,6aR)-6-(5-fluoro-2-nitro-phenoxy)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol

Product 1

HCID 86718452(3R,3aR,6R,6aR)-6-(5-fluoro-2-nitro-phenoxy)-3-methoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

To 0.9 g (3.0 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), 0.1 g (0.3 mmol) tetrabutylammonium iodide and 1.3 ml (7.8 mmol) of a 6 mol/l aqueous NaOH solution in 15 ml DCM 0.3 ml (3.6 mmol) dimethyl sulfate are added dropwise and the mixture is stirred at RT for 24 h. Additional 1.3 ml (7.8 mmol) of a aqueous 6 mol/l NaOH solution and 0.3 ml (3.6 mml) dimethyl sulfate are added and the mixture is stirred at RT over night. The reaction mixture is washed with water, dried and evaporated. The residue is purified by FC.

Workup

  1. stirringthe mixture is stirred at RT over night
  2. washThe reaction mixture is washed with water
  3. customdried
  4. customevaporated
  5. customThe residue is purified by FC

Sources & evidence

ORD record
ord-803fb7a6fb5a4665a0a1720f0942ccd3
Source dataset
uspto-grants-2014_12
Patent number
US08901138B2

Reaction notes

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