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

HRID 1396635
Notes
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Reaction equation

HRID 1396635 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH2:12]1[O:16][C@@H:15]2[C@H:17]([OH:20])[CH2:18][O:19][C@@H:14]2[C@@H:13]1[OH:21].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.Cl>C1COCC1>[F:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([CH:7]=1)[O:21][C@H:13]1[C@H:14]2[O:19][CH2:18][C@@H:17]([OH:20])[C@H:15]2[O:16][CH2:12]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 679672,4-DifluoronitrobenzeneHCID 2733832Lithium hexamethyldisilazaneHCID 109756241,4:3,6-Dianhydro-D-mannitol

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

2.2 ml (20.0 mmol) 2,4-difluoro-1-nitro-benzene and 2.9 g (20.0 mmol) 1,4:3,6-dianhydro-D-mannitol in 70 ml THF are cooled to −5° C. 20 ml (20.0 mml) 1M LiHMDS in THF are added dropwise and the reaction mixture is allowed to warm to RT and stirred over night. 1M HCl is added and the mixture is extracted with EtOAc. The organic phases are pooled and washed with water, dried and evaporated. The residue is purified by FC.

Workup

  1. extractionthe mixture is extracted with EtOAc
  2. washwashed with water
  3. customdried
  4. customevaporated
  5. customThe residue is purified by FC

Sources & evidence

ORD record
ord-77e413ac1a06437eace0a97dce5255e0
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08901138B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes