Pyridine → HCID 54090850, compound

HRID 880429Notes

Reaction equation

HRID 880429 reaction equation
[CH:1]1([CH2:5]O)[CH2:4][CH2:3][CH2:2]1.[CH2:7]([O:9][C:10]([CH:12]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:11])[CH3:8].N1C=CC=CC=1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH:1]1([CH:5]=[CH:12][C:10]([O:9][CH2:7][CH3:8])=[O:11])[CH2:2][CH2:3][CH2:4]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 78130Cyclobutylcarbinol

Product 1

HCID 54090850HCID 54090850, compoundYield 24.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of cyclobutyl-methanol (8.00 g, 93.02 mmol), ethoxycarbonylmethylene triphenylphosphorane (19.42 g, 55.81 mmol) and pyridine (3 mL) were dissolved in dry chloroform (100 mL) and heated at 70° C. Manganese dioxide (97.11 g, 1.12 mol) was added portion wise over a period of 5 h (with 1 h gap between each addition) and refluxing was continued for 20 h. The reaction mixture was cooled to room temperature, filtered over celite and washed with chloroform. The filtrate was concentrated and the residue subjected to column chromatography over silica gel (60-120 mesh) using 0% to 15% of ethyl acetate in pet ether as eluent to afford ethyl 3-cyclobutylprop-2-enoate (2.10 g, 15%) as a liquid.

Workup

  1. additionbetween each addition) and
  2. temperaturerefluxing
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationfiltered over celite
  5. washwashed with chloroform
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-669df45cad824e93be8df565a7f654b5
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

Loading…