Water → HCID 11545669, compound

HRID 1876475Notes

Reaction equation

HRID 1876475 reaction equation
O[Li].O.O.C([O:9][C:10]([C:12]1([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22](=[O:40])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]2([C:33]([O:35]CCCC)=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29]2)[CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11])CCC>CCO>[C:33]([C:28]1([CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][C:22](=[O:40])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][C:12]2([C:10]([OH:11])=[O:9])[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH2:29][CH2:30][CH2:31][CH2:32]1)([OH:35])=[O:34]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 21932042HCID 21932042, compound

Product 1

HCID 11545669HCID 11545669, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

LiOH.H2O (7.83 g, 187 mmol) and H2O (100 mL) were added to a solution of butyl 1-{11-[1-(butoxycarbonyl)cyclopentyl]-6-oxoundecyl}-1-cyclopentanecarboxylate (21.03 g, 90% pure by 1H NMR, 37.3 mmol) in EtOH (300 mL) and the resulting mixture was stirred at reflux temperature for 2 d, allowed to cool to rt and concentrated in vacuo to a smaller volume. H2O (100 mL) was added and the resulting mixture was extracted with Et2O (100 mL), acidified with conc aqueous HCl (25 mL) and extracted with Et2O (3×150 mL). The latter organic layers were combined, dried (Na2SO4; To avoid loss of material, a minimal amount of Na2SO4 was used, with the desiccant becoming a white, oily paste. The organic layer was decanted from the desiccant.) and evaporated in vacuo. The remaining residue was purified by recrystallization from a mixture of iPr2O and heptane to give 1-[11-(1-carboxycyclopentyl)-6-oxoundecyl]-1-cyclopentanecarboxylic acid (12.15 g, 83%) as white granules. mp=78-85° C. 1H NMR (CDCl3): δ=2.37 (t, J=7.4 Hz, 4H), 2.18-2.10 (m, 4H), 1.65-1.45 (m, 20H), 1.29-1.25 (m, 8H). 13C NMR (CDCl3): δ=211.5, 184.8 (2×), 54.0 (2×), 42.4 (2×), 38.9 (2×), 35.9 (4×), 29.2 (2×), 25.5 (2×), 24.9 (4×), 23.5 (2×). Anal. calcd for C23H38O5: C, 70.02; H, 9.71, found: C, 70.37; H, 9.72.

Workup

  1. temperatureat reflux temperature for 2 d
  2. concentrationconcentrated in vacuo to a smaller volume
  3. additionH2O (100 mL) was added
  4. extractionthe resulting mixture was extracted with Et2O (100 mL)
  5. extractionextracted with Et2O (3×150 mL)
  6. dry with materialdried (Na2SO4
  7. customThe organic layer was decanted from the desiccant
  8. custom) and evaporated in vacuo
  9. customThe remaining residue was purified by recrystallization from a mixture of iPr2O and heptane

Sources & evidence

ORD record
ord-75143fe29bbe44d3aaa0a4d921ef5728
Source dataset
uspto-grants-2012_11
Patent number
US08309604B2

Reaction notes

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