Trimethylsilyl isocyanate → naphtho[1,2-b]furan-3(2H)-one

HRID 847236Notes

Reaction equation

HRID 847236 reaction equation
[O:1]1[CH:5](NC(=O)NO)[CH2:4][C:3]2[CH:11]=[CH:12][C:13]3[C:18]([C:2]1=2)=[CH:17][CH:16]=[CH:15][CH:14]=3.C[Si](N=C=[O:25])(C)C>C1COCC1>[O:1]1[CH2:5][C:4](=[O:25])[C:3]2[CH:11]=[CH:12][C:13]3[C:18]([C:2]1=2)=[CH:17][CH:16]=[CH:15][CH:14]=3

Participants

4

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 867460753-(2,3-Dihydronaphtho[1,2-b]furyl}-N-hydroxyurea

Product 1

HCID 1471593naphtho[1,2-b]furan-3(2H)-oneYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

N-{3-(2,3-Dihydronaphtho[1,2-b]furyl}-N-hydroxyurea. To a solution of N-{3-(2,3-dihydronaphtho[1,2-b]furyl}-N-hydroxyamine (72 mg, 0.36 mmol) in THF (4 mL) was added trimethylsilylisocyanate (98 μL, 0.72 mmol). The resulting solution was heated at 60° C. for 1 h, then allowed to cool and concentrated under reduced pressure. The residue was dissolved in EtOAC and washed successively with H2O and saturated aqueous NaCl. The solvent was removed in vacuo, and the residue was triturated with Et2O. The solid residue was purified by flash chromatography, eluting with 3% MeOH/CH2Cl2 and recrystallized from MeOH/CH2Cl2 to provide the title compound (31 mg, 35%). m.p. 191°-192° C.

Workup

  1. temperatureto cool
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in EtOAC
  4. washwashed successively with H2O and saturated aqueous NaCl
  5. customThe solvent was removed in vacuo
  6. customthe residue was triturated with Et2O
  7. customThe solid residue was purified by flash chromatography
  8. washeluting with 3% MeOH/CH2Cl2
  9. customrecrystallized from MeOH/CH2Cl2

Sources & evidence

ORD record
ord-c987f8c188204da6930976eec94e6da0
Source dataset
uspto-grants-1992_08
Patent number
US05140047

Reaction notes

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