Diethyl Ether → HCID 10728977, compound

HRID 972223Notes

Reaction equation

HRID 972223 reaction equation
[C:1](=O)([O:5]CC)[O:2][CH2:3][CH3:4].CCOCC.[H-].[Na+].[CH3:16][C:17]1([CH2:22][CH2:23][CH2:24][C:25](=[O:27])[CH3:26])[O:21][CH2:20][CH2:19][O:18]1>CCCCCC.C(O)C>[CH2:3]([O:2][C:1](=[O:5])[CH2:26][C:25](=[O:27])[CH2:24][CH2:23][CH2:22][C:17]1([CH3:16])[O:18][CH2:19][CH2:20][O:21]1)[CH3:4]

Participants

7

Reactant 4

HCID 3283Diethyl Ether2×HCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 104196285-(2-Methyl-1,3-dioxolan-2-yl)-2-pentanone

Product 1

HCID 10728977HCID 10728977, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8058HexaneSolvent

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 per cent 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. (0.5 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 1/2hours. 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. customdried under nitrogen
  2. temperatureA gentle reflux
  3. temperaturewas maintained throughout the addition
  4. waitthe refluxing was continued for an additional period of approximately 1 1/2hours
  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-c2dc6e2fabca4d818c1edf19d5126eaf
Source dataset
uspto-grants-1977_10
Patent number
US04052413

Reaction notes

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