3-Furanol, tetrahydro- → 4-Nitro-3-(tetrahydrofuran-3-yloxy)-benzamide

HRID 472016Notes

Reaction equation

HRID 472016 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][O:4][CH2:3]1.[H-].[Na+].F[C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20])[C:13]([NH2:15])=[O:14]>C1COCC1>[N+:19]([C:18]1[CH:10]=[CH:11][C:12]([C:13]([NH2:15])=[O:14])=[CH:16][C:17]=1[O:1][CH:2]1[CH2:6][CH2:5][O:4][CH2:3]1)([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 99603-Furanol, tetrahydro-HCID 24758Sodium hydrideHCID 114239673-Fluoro-4-nitrobenzamide

Product 1

HCID 592259634-Nitro-3-(tetrahydrofuran-3-yloxy)-benzamideYield 99.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 3-hydroxytetrahydrofuran (2.57 ml, 1.2 eq, 23.0 mmol) in THF (50 ml) was added sodium hydride as a 60% dispersion in oil (0.84 g, 1.1 eq, 20.91 mmol) this mixture was then stirred at 0° C. for 30 minutes. The preceding mixture was added dropwise to a solution of 3-fluoro-4-nitrobenzamide (3.5 g, 1.0 eq, 19.01 mmol) in THF (30 ml) and stirred at room temperature for 3.5 hours. The reaction was quenched with water and extracted with DCM (3×50 ml), the organics were combined, dried over sodium sulphate, filtered and the solvent removed in vacuo to give the title compound as a yellow solid (4.77 g, 18.9 mmol, 96% corrected). LCMS: [M+H]+=253, Rt=1.41 min, 100% purity

Workup

  1. stirringstirred at room temperature for 3.5 hours
  2. customThe reaction was quenched with water
  3. extractionextracted with DCM (3×50 ml)
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-135f36d1c0154fe0bfaf0b2ece4141db
Source dataset
uspto-grants-2014_01
Patent number
US08633201B2

Reaction notes

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