Allyl Alcohol → ALLYL 2-OXOCYCLOPENTANECARBOXYLATE

HRID 590688Notes

Reaction equation

HRID 590688 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

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 treated with powdered zinc (0.40 g, 6 mmol), refluxed for 48 h, and cooled to room temperature. The suspension was filtered, the filter cake rinsed with toluene, and the filtrate 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. temperaturerefluxed for 48 h
  2. filtrationThe suspension was filtered
  3. washthe filter cake rinsed with toluene
  4. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-061a63d88ef6459592c6b29951add2b2
Source dataset
uspto-grants-2016_01
Patent number
US09233985B2

Reaction notes

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