Cyclopentanecarboxylic acid → HCID 86598001, compound

HRID 2101246Notes

Reaction equation

HRID 2101246 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-c6f670581d9a4bbf92cc13ce31659dcb
Source dataset
uspto-grants-2009_08
Patent number
US07572830B2

Reaction notes

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