1-Cyclopropylethanol → 3-(1-cyclopropylethoxy)-4-hydroxy-2(5H)-furanone

HRID 1602548Notes

Reaction equation

HRID 1602548 reaction equation
[N+](=[C:3]1[C:7](=[O:8])[CH2:6][O:5][C:4]1=[O:9])=[N-].[CH3:10][CH:11]([CH:13]1[CH2:15][CH2:14]1)[OH:12]>C([O-])(=O)C.[Rh+3].C([O-])(=O)C.C([O-])(=O)C>[CH:13]1([CH:11]([O:12][C:3]2[C:4](=[O:9])[O:5][CH2:6][C:7]=2[OH:8])[CH3:10])[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 791041-CyclopropylethanolHCID 154391133-Diazofuran-2,4-dione

Product 1

HCID 701064543-(1-cyclopropylethoxy)-4-hydroxy-2(5H)-furanone

Reagents, catalysts & solvents 1

HCID 168478Rhodium acetateCatalyst

Conditions

Temperature
130 °C

Procedure

To the mixture of 3-diazo-2,4-(3H, 5H)-furandione (300 mg, 2.38 mmol; Example 207, Step 1) and α-methylcyclopropanemethanol (2.0 mL) was added rhodium acetate (30 mg). The mixture was heated at 130° C. for a period of 18 h. The excess of alcohol was evaporated under reduced pressure and the resulting crude mixture was purified by flash chromatography (10% to 20% MeOH in CH2Cl2) to provide 50 mg of the title compound.

Workup

  1. customThe excess of alcohol was evaporated under reduced pressure
  2. customthe resulting crude mixture was purified by flash chromatography (10% to 20% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-1ad36e16705846fbb2bf4c5139b3d46a
Source dataset
uspto-grants-1999_11
Patent number
US05981576

Reaction notes

Loading…