Sodium Methoxide → HCID 90021327, compound

HRID 1488173Notes

Reaction equation

HRID 1488173 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([C:6](=[O:9])[CH2:7][CH3:8])[CH2:2]1.[CH3:10][O-:11].[Na+]>C(OCC)=O>[CH3:8][CH:7]([C:6](=[O:9])[CH:3]1[CH2:4][CH2:5][O:1][CH2:2]1)[CH:10]=[O:11]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 21702750HCID 21702750, compound2×

Product 1

HCID 90021327HCID 90021327, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8025Ethyl formateSolvent

Procedure

Into a 100-mL round-bottom flask, was placed 1-(tetrahydrofuran-3-yl)propan-1-one (compound 263.2, 2.5 g, 19.5 mmol), sodium methoxide (1.4 g, 25.9 mmol) and ethyl formate (20 mL). The mixture was stirred overnight at room temperature, then concentrated under reduced pressure. The residue was purified by a silica gel column chromatography with ethyl acetate/petroleum ether (1:20 to 1:5) as eluent to obtain the title compound as a yellow solid (2.0 g, 66%).

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by a silica gel column chromatography with ethyl acetate/petroleum ether (1:20 to 1:5) as eluent

Sources & evidence

ORD record
ord-3ab0b34df5c24500a7d02cc7d3e1aad8
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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