Ethyl formate → HCID 67870812, compound

HRID 569895Notes

Reaction equation

HRID 569895 reaction equation
[CH2:1]1[O:11][C:4]2([CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]2)[O:3][CH2:2]1.[H-].[Na+].[CH:14](OCC)=[O:15]>C(O)C.O1CCCC1>[OH:15][CH:14]=[C:8]1[C:7](=[O:10])[CH2:6][CH2:5][C:4]2([O:3][CH2:2][CH2:1][O:11]2)[CH2:9]1

Participants

6

Reactant 3

HCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 5674151,4-Dioxaspiro[4.5]decan-8-one

Product 1

HCID 67870812HCID 67870812, compound

Reagents, catalysts & solvents 2

HCID 702EthanolCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1,4-Cyclohexanedione monoethylene ketal (5.00 g) was added to a mixture of sodium hydride (1.40 g of a 60% suspension in mineral oil), 10 ml of ethyl formate, 1 drop of ethanol and 200 ml of tetrahydrofuran. The reaction mixture was heated at reflux for 2.5 hours, cooled and partitioned between water and ethyl ether. The ethereal layer was extracted several times with 0.5N sodium hydroxide and the combined aqueous portions were washed once with ether. The aqueous solution was acidified slowly to a pH of 4 with 5N hydrochloric acid and the slurry was exhaustively extracted with dichloromethane. The combined extracts were dried over magnesium sulfate and concentrated in vacuo to provide a dark oil. The oil was distilled bulb-to-bulb (120° C./lmm) to afford 7-(hydroxymethylene)-1,4-dioxaspiro-[4.5]decan-8-one as a colorless oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2.5 hours
  3. temperaturecooled
  4. custompartitioned between water and ethyl ether
  5. extractionThe ethereal layer was extracted several times with 0.5N sodium hydroxide
  6. washthe combined aqueous portions were washed once with ether
  7. extractionthe slurry was exhaustively extracted with dichloromethane
  8. dry with materialThe combined extracts were dried over magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customto provide a dark oil
  11. distillationThe oil was distilled bulb-to-bulb (120° C./lmm)

Sources & evidence

ORD record
ord-ead8602fd2db4450baefd45de479dd26
Source dataset
uspto-grants-1988_03
Patent number
US04734429

Reaction notes

Loading…