Diethyl Ether → HCID 10728977, compound

HRID 1439422Notes

Reaction equation

HRID 1439422 reaction equation
[C:1](=O)([O:5]CC)[O:2][CH2:3][CH3:4].CCOCC.[CH3:14][C:15]1([CH2:20][CH2:21][CH2:22][C:23](=[O:25])[CH3:24])[O:19][CH2:18][CH2:17][O:16]1>C(O)C>[CH2:3]([O:2][C:1](=[O:5])[CH2:24][C:23](=[O:25])[CH2:22][CH2:21][CH2:20][C:15]1([CH3:14])[O:16][CH2:17][CH2:18][O:19]1)[CH3:4]

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 7766Diethyl CarbonateHCID 104196285-(2-Methyl-1,3-dioxolan-2-yl)-2-pentanone

Product 1

HCID 10728977HCID 10728977, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

11.8 Grams (0.1 moles) of diethyl carbonate in 12.5 ml. of anhydrous ether was added to 4.55 g. (0.1 moles) of a 53 percent dispersion of sodium hydride in mineral oil which was washed with anhydrous hexane and dried under nitrogen. This mixture was stirred under nitrogen and 8.6 g. (0.55 mole) of the ketal ketone, 5-(2-methyl-1,3-dioxolan-2-yl)-2-pentanone was added dropwise over a period of two hours. A gentle reflux was maintained throughout the addition and the refluxing was continued for an additional period of approximately 11/2 hours. The solution was then cooled with an ice bath, 20 ml. of anhydrous ether and 2 ml. of absolute ethyl alcohol was added and it was stirred for 45 minutes to destroy any unreacted sodium hydride. The suspension was diluted with an equal volume of ether and the ice cold suspension was then added to a rapidly agitated mixture of 6 ml. of glacial acetic acid and 200 ml. of ice water. The etheral layer was separated, and the aqueous layer was additionally extracted twice with ether. The extract was washed with saturated sodium bicarbonate and with a saturated sodium chloride, dried with sodium sulfate, filtered and evaporated in vacuo to give the crude β-keto ester, 6-(2-methyl-1,3-dioxolan-2-yl)-3-oxo-hexanoic acid ethyl ester, b.p. 110°-112° C at 0.2 mm.,

Workup

  1. wash(0.1 moles) of a 53 percent dispersion of sodium hydride in mineral oil which was washed with anhydrous hexane
  2. customdried under nitrogen
  3. temperatureA gentle reflux
  4. temperaturewas maintained throughout the addition
  5. waitthe refluxing was continued for an additional period of approximately 11
  6. custom2 hours
  7. temperatureThe solution was then cooled with an ice bath
  8. stirringit was stirred for 45 minutes
  9. customto destroy any unreacted sodium hydride
  10. additionThe suspension was diluted with an equal volume of ether
  11. additionthe ice cold suspension was then added to a rapidly agitated mixture of 6 ml
  12. customThe etheral layer was separated
  13. extractionthe aqueous layer was additionally extracted twice with ether
  14. washThe extract was washed with saturated sodium bicarbonate and with a saturated sodium chloride
  15. dry with materialdried with sodium sulfate
  16. filtrationfiltered
  17. customevaporated in vacuo

Sources & evidence

ORD record
ord-a439fcb67045437186b1927d54c512b1
Source dataset
uspto-grants-1977_11
Patent number
US04059612

Reaction notes

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