Cyclopentanecarboxylic acid → HCID 86598001, compound

HRID 2215289Notes

Reaction equation

HRID 2215289 reaction equation
[C:1](=[O:12])([S:9][CH2:10][CH3:11])[O:2][O:3][CH:4](Cl)[CH2:5][CH2:6][CH3:7].[CH:13]1([C:18]([OH:20])=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14]1>>[C:1](=[O:12])([S:9][CH2:10][CH3:11])[O:2][O:3][CH:4]([O:20][C:18]([CH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:19])[CH2:5][CH2:6][CH3:7]

Participants

3

Reactant 2

HCID 18840Cyclopentanecarboxylic acidHCID 86598002HCID 86598002, compound

Product 1

HCID 86598001HCID 86598001, compoundYield 86%

Conditions

Temperature
75 °C

Procedure

A mixture of (66) (1.33 g, 6.76 mmol) and cyclopentancarboxylic acid (1.30 g, 10.1 mmol) was stirred at 75° C. for five days. The reaction was then cooled to room temperature and partitioned between water and ether. The ether layer was washed with brine, dried over anhydrous Na2SO4. Filtration then removal of the solvent by rotary evaporation gave the title thiocarbonate (67) (1.62 g, 86%). 1H NMR (CDCl3, 400 MHz): δ 0.95 (t, 3H), 1.20–1.85 (m, 15H), 2.68 (m, 1H), 2.82 (m, 2H). 6.84 (t, 1H).

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. custompartitioned between water and ether
  3. washThe ether layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationFiltration
  6. customremoval of the solvent
  7. customby rotary evaporation

Sources & evidence

ORD record
ord-c30cb2dad9124df2856db13a7d786584
Source dataset
uspto-grants-2006_09
Patent number
US07109239B2

Reaction notes

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