Diethyl Ether → HCID 10728977, compound

HRID 1678914Notes

Reaction equation

HRID 1678914 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. (0.05 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 1 1/2 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., Analysis calculated for C12H20O5 : C, 59.00; H, 8.25. Found: C, 58.92; H, 8.38.

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. temperatureThe solution was then cooled with an ice bath
  6. stirringit was stirred for 45 minutes
  7. customto destroy any unreacted sodium hydride
  8. additionThe suspension was diluted with an equal volume of ether
  9. additionthe ice cold suspension was then added to a rapidly agitated mixture of 6 ml
  10. customThe etheral layer was separated
  11. extractionthe aqueous layer was additionally extracted twice with ether
  12. washThe extract was washed with saturated sodium bicarbonate and with a saturated sodium chloride
  13. dry with materialdried with sodium sulfate
  14. filtrationfiltered
  15. customevaporated in vacuo

Sources & evidence

ORD record
ord-a8f4435dd86f4e7faa95a8d4f8e02eeb
Source dataset
uspto-grants-1978_03
Patent number
US04077983

Reaction notes

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