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

HRID 847239Notes

Reaction equation

HRID 847239 reaction equation
[CH:1]1(N(O)C(N)=O)[CH2:5][O:4][C:3]2[CH:6]=[CH:7][C:8]3[C:13]([C:2]1=2)=[CH:12][CH:11]=[CH:10][CH:9]=3.C[Si](N=C=[O:25])(C)C>C1COCC1>[C:1]1(=[O:25])[CH2:5][O:4][C:3]2[CH:6]=[CH:7][C:8]3[C:13]([C:2]1=2)=[CH:12][CH:11]=[CH:10][CH:9]=3

Participants

4

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 10752791HCID 10752791, compound

Product 1

HCID 1471585naphtho[2,1-b]furan-1(2H)-oneYield 11%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

N-{1-(1,2-Dihydronaphtho[2,1-b]furyl}-N-hydroxyurea. To a solution of N-{1-(1,2-dihydronaphtho[2,1-b]furyl}-N-hydroxyamine (698 mg, 3.5 mmol) in THF (10 mL) was added trimethylsilylisocyanate (0.94 mL, 7.0 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. The residue was triturated with Et2O and recrystallized from MeOH/CH2Cl2 /hexanes to provide the title compound (93 mg, 11%). m.p. 194.5°-195.5° 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. customrecrystallized from MeOH/CH2Cl2 /hexanes

Sources & evidence

ORD record
ord-e797aee85fce4794a4bf269eb4731805
Source dataset
uspto-grants-1992_08
Patent number
US05140047

Reaction notes

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