Allyl Alcohol → ALLYL 2-OXOCYCLOPENTANECARBOXYLATE

HRID 1498973Notes

Reaction equation

HRID 1498973 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]([O:9][CH3:10])=[O:8].[CH2:11](O)[CH:12]=C>C1(C)C=CC=CC=1.[Zn]>[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]([O:9][CH2:10][CH:11]=[CH2:12])=[O:8]

Participants

5

Reactant 2

HCID 7858Allyl AlcoholHCID 66328Cyclopentanecarboxylic acid, 2-oxo-, methyl ester

Product 1

HCID 11008303ALLYL 2-OXOCYCLOPENTANECARBOXYLATEYield 99.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 1140TolueneSolvent

Procedure

To a stirred solution of methyl 2-oxocyclopentanecarboxylate (4.26 g, 30 mmol) and allyl alcohol (10.2 mL, 150 mmol) in anhydrous toluene (25 mL) was added powdered zinc (0.40 g, 6 mmol). After refluxing the mixture for 48 h, it was cooled to room temperature and the suspension was filtered. The filter cake was rinsed with toluene and the combined filtrate was concentrated to afford allyl 2-oxocyclopentanecarboxylate (5.01 g, 99%) as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ 5.89 (ddt, J1=15.9 Hz, J2=10.5 Hz, J3=4.8 Hz, 1 H), 5.33 (dtd, J1=15.9 Hz, J2=2.7 Hz, J3=1.4 Hz, 1 H), 5.23 (dtd, J1=10.5 Hz, J2=2.7 Hz, J3=1.4 Hz, 1 H), 4.83-4.75 (m, 1 H), 3.18 (t, J=9.0 Hz, 1 H), 2.41-2.23 (m, 4 H), 2.22-2.07 (m, 1 H), 1.94-1.80 (m, 1 H); MS (+CI): m/z for C9H12O3: expected 168.1; found 169.1 (M+H)+.

Workup

  1. temperatureAfter refluxing the mixture for 48 h
  2. filtrationthe suspension was filtered
  3. washThe filter cake was rinsed with toluene
  4. concentrationthe combined filtrate was concentrated

Sources & evidence

ORD record
ord-4bb5876f629b4fc597aa3e7ee0c1a3d9
Source dataset
uspto-grants-2015_12
Patent number
US09200011B2

Reaction notes

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