Methyl acetoacetate → Non-1-en-3-one

HRID 1706007Notes

Reaction equation

HRID 1706007 reaction equation
[CH:1](=[C:4]1[CH2:8][CH2:7][CH2:6][C:5]1=[O:9])[CH2:2]C.[Na].[C:11](OC)(=O)[CH2:12]C(C)=O>CO>[CH2:11]=[CH:12][C:5](=[O:9])[CH2:6][CH2:7][CH2:8][CH2:4][CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 30161952-PropylidenecyclopentanoneHCID 5360545Sodium

Product 1

HCID 181106Non-1-en-3-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The procedure of Example 1 is repeated with 19.5 g (0.16 mol) of propylidene cyclopentanone, 0.46 g (0.02 g-atom) of sodium, 21 g (0.18 mol) of methyl acetoacetate and 100 ml of methanol. Fractional distillation yields 14 g (bp 95°-102° C. at 0.5 mm) of 5-ethylbicyclo [4.3.0.] non-1-en-3-one having the structure: ##STR8##

Workup

  1. distillationFractional distillation

Sources & evidence

ORD record
ord-635e6c77978d449291fac4ce91871fe4
Source dataset
uspto-grants-1980_06
Patent number
US04206089

Reaction notes

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