Tetrahydrofuran → 4-[(1-Ethoxy)ethoxy]cinnamyl acetoacetate

HRID 846635

Reaction equation

HRID 846635 reaction equation
[C:1]([CH:4]1[C:9](=[O:10])[O:8][C:7]([CH3:12])(C)OC1=O)(=[O:3])[CH3:2].C(O[CH:17]([O:19][C:20]1[CH:29]=[CH:28][C:23]([CH:24]=CCO)=[CH:22][CH:21]=1)[CH3:18])C.[O:30]1CC[CH2:32][CH2:31]1>>[C:9]([O:8][CH2:7][CH:12]=[CH:24][C:23]1[CH:22]=[CH:21][C:20]([O:19][CH2:17][CH2:18][O:30][CH2:31][CH3:32])=[CH:29][CH:28]=1)(=[O:10])[CH2:4][C:1]([CH3:2])=[O:3]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 27634705-Acetyl-2,2-dimethyl-1,3-dioxane-4,6-dioneHCID 537865114-(1-Ethoxyethoxy)cinnamyl alcohol

Product 1

HCID 542124814-[(1-Ethoxy)ethoxy]cinnamyl acetoacetate

Procedure

18.6 Grams of 5-acetyl-2,2-dimethyl-1,3-dioxane-4,6-dione and 50 ml tetrahydrofuran solution containing 22.2 g of 4-(1-ethoxyethoxy)cinnamyl alcohol were refluxed for 6 hours. After the reaction was completed, the solvent was removed by evaporation, and the residue thus obtained was purified by means of a silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:4) to yield 5.8 g of 4-[(1-ethoxy)ethoxy]cinnamyl acetoacetate as in the form of an oily substance.

Workup

  1. temperaturewere refluxed for 6 hours
  2. customthe solvent was removed by evaporation
  3. customthe residue thus obtained
  4. customwas purified by means of a silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:4)

Sources & evidence

ORD record
ord-22419b93506b4b23b6320e7ca1b268c8
Source dataset
uspto-grants-1992_08
Patent number
US05137889

Linked notes

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