Gamma-Butyrolactone → HCID 66632760, compound

HRID 1619386Notes

Reaction equation

HRID 1619386 reaction equation
[H-].[Na+:2].[O:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8].[CH:9](OCC)=[O:10]>CCCCCC.CCOCC>[O:8]=[C:4]1[C:5](=[CH:9][O-:10])[CH2:6][CH2:7][O:3]1.[Na+:2]

Participants

6

Reactant 3

HCID 7302Gamma-ButyrolactoneHCID 8025Ethyl formateHCID 24758Sodium hydride

Product 1

HCID 66632760HCID 66632760, compoundYield 102.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent3×HCID 8058HexaneSolvent

Procedure

Three-neck, round-bottomed flask equipped with mechanical stirrer, addition funnel, and reflux condenser was placed in a hood behind a shield. The condenser was fitted with a drying tube which was connected to a mineral oil bubble chamber so hydrogen evolution could be monitored. After NaH (4.4 g of 60% oil dispersion, 0.11 mol) was washed with n-C6H14 (2×50 mL), filtered with brief suction drying, and transferred to the flask, sufficient Et2O was added to cover the resulting solid. A catalytic amount of C2H5OH (ca. 2 drops) was added directly to the Et2O—NaH suspension and dropwise addition without stirring of a solution of dihydrofuran-2(3H)-one (8.61 g, 0.1 mol) and ethyl formate (7.41 g, 0.1 mol) in Et2O (10 mL) was started. As soon as the Et2O began to reflux, additional Et2O (50-60 mL) was rapidly added through the reflux condenser and stirring was started. Lactone-formate addition was complete in 1 hr, and stirring was continued for an additional 22 h. Filtration, washing with Et2O, and vacuum drying gave desired product (14.0 g) as a fine powdery solid.

Workup

  1. customThree-neck, round-bottomed flask equipped with mechanical stirrer, addition funnel
  2. temperaturereflux condenser
  3. customThe condenser was fitted with a drying tube which
  4. custombubble chamber so hydrogen evolution
  5. filtrationfiltered with brief suction
  6. customdrying
  7. additionwas added
  8. additionA catalytic amount of C2H5OH (ca. 2 drops) was added directly to the Et2O—NaH suspension and dropwise addition
  9. temperatureto reflux
  10. stirringstirring
  11. waitwas continued for an additional 22 h
  12. filtrationFiltration
  13. washwashing with Et2O, and vacuum
  14. customdrying

Sources & evidence

ORD record
ord-90e04eea5d0148a79723b7e7db363b8c
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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