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

HRID 1396643Notes

Reaction equation

HRID 1396643 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.[CH2:21](I)[CH3:22].[H-].[Na+].O>CN(C=O)C.CCOC(C)=O>[CH2:21]([O:16][C@@H:15]1[CH2:14][O:13][C@@H:12]2[C@H:8]([O:7][C:6]3[CH:17]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=3[N+:18]([O-:20])=[O:19])[CH2:9][O:10][C@H:11]12)[CH3:22]

Participants

7

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 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 86718463(3R,3aR,6R,6aR)-3-ethoxy-6-(5-fluoro-2-nitro-phenoxy)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  1. customis kept below 35° C
  2. customthe organic layer is separated
  3. washwashed with water
  4. customdried
  5. customevaporated
  6. customThe residue was purified by FC

Sources & evidence

ORD record
ord-ab315cd7c72d4d29a800f052cb3c5dcd
Source dataset
uspto-grants-2014_12
Patent number
US08901138B2

Reaction notes

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