Pivalic acid → Methyl 3-oxo-2-pentylidenecyclopentaneacetate

HRID 1784133Notes

Reaction equation

HRID 1784133 reaction equation
O[CH:2]([C:7]1[C:8](=[O:12])[CH2:9][CH2:10][CH:11]=1)[CH2:3][CH2:4][CH2:5][CH3:6].[C:13]([OH:19])(=[O:18])[C:14](C)(C)C.[CH3:20]C(C)(C)C([O-])([O-])[O-]>CO>[O:12]=[C:8]1[CH2:9][CH2:10][CH:11]([CH2:14][C:13]([O:19][CH3:20])=[O:18])[C:7]1=[CH:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 6417Pivalic acidHCID 11636872HCID 11636872, compoundHCID 21927715Trimethylorthoacetate

Product 1

HCID 57354385Methyl 3-oxo-2-pentylidenecyclopentaneacetateYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(1-hydroxypentyl)-2-cyclopenten-1-one (720 mg, 4.2 mmol) and pivalic acid (100 mg, 0.98 mmol) in trimethylorthoacetate (5 ml, 39.3 mmol) was heated at 115° C. for 3 hours with distillation of MeOH. The concentrated reaction mixture was bulb-to-bulb distilled to afford the title compound in 88% yield and in the form of a 66:34 (Z)/(E) mixture.

Workup

  1. customThe concentrated reaction mixture
  2. distillationdistilled

Sources & evidence

ORD record
ord-157c9ed3dcb14c5a90079d5afbbf6d01
Source dataset
uspto-grants-2009_03
Patent number
US07501539B2

Reaction notes

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