Stannous chloride dihydrate → HCID 117095589, compound

HRID 2281085Notes

Reaction equation

HRID 2281085 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:17]([O-])=O)=[C:6]([CH:16]=1)[O:7][CH:8]([C:10]1[O:14][N:13]=[C:12]([CH3:15])[CH:11]=1)[CH3:9].O.O.[Sn](Cl)Cl>CCOC(C)=O.[OH-].[Na+]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:17])=[C:6]([O:7][CH:8]([C:10]2[O:14][N:13]=[C:12]([CH3:15])[CH:11]=2)[CH3:9])[CH:16]=1

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 117772713HCID 117772713, compound

Product 1

HCID 117095589HCID 117095589, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

6.61 g (24.84 mmol) 5-[1-(5-fluoro-2-nitro-phenoxy)ethyl]-3-methyl-isoxazole and 24.66 g (109.30 mmol) tin(II)chloride dihydrate in EtOAc are stirred for 1 h at reflux. The mixture is diluted with 180 mL EtOAc and 180 mL aq. NaOH (4M). The organic layer is separated and the aqueous layer is extracted with EtOAc. The combined organic layers are washed with water and brine, separated, dried and evaporated. The residue is purified by FC.

Workup

  1. temperatureat reflux
  2. customThe organic layer is separated
  3. extractionthe aqueous layer is extracted with EtOAc
  4. washThe combined organic layers are washed with water and brine
  5. customseparated
  6. customdried
  7. customevaporated
  8. customThe residue is purified by FC

Sources & evidence

ORD record
ord-8903ed5dd8014802a0c127b75864e770
Source dataset
uspto-grants-2015_09
Patent number
US09139577B2

Reaction notes

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