Water → HCID 11702831, compound

HRID 1469887Notes

Reaction equation

HRID 1469887 reaction equation
O[Li].O.O.C([O:7][C:8]([C:10]1([CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:32])[CH2:19][CH2:20][CH2:21][CH2:22][C:23]2([C:27]([O:29]CC)=[O:28])[CH2:26][CH2:25][CH2:24]2)[CH2:13][CH2:12][CH2:11]1)=[O:9])C>CCO>[C:27]([C:23]1([CH2:22][CH2:21][CH2:20][CH2:19][C:18](=[O:32])[CH2:17][CH2:16][CH2:15][CH2:14][C:10]2([C:8]([OH:9])=[O:7])[CH2:11][CH2:12][CH2:13]2)[CH2:26][CH2:25][CH2:24]1)([OH:29])=[O:28]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 21069430HCID 21069430, compound

Product 1

HCID 11702831HCID 11702831, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

LiOH.H2O (3.94 g, 93.9 mmol) and H2O (30 mL) were added to a solution of ethyl 1-9-[1-(ethoxycarbonyl)cyclobutyl]-5-oxononyl-1-cyclobutanecarboxylate (9.20 g, 23.3 mmol) in EtOH (90 mL) and the resulting mixture was stirred at reflux temperature for 17 h, allowed to cool to rt and concentrated in vacuo to a smaller volume. H2O (150 mL) was added and the resulting mixture was extracted with Et2O (50 mL), acidified with aqueous HCl (6 M, 25 mL) and extracted with Et2O (1×100 mL, 2×50 mL). The latter organic layers were combined, washed with brine (50 mL), dried (Na2SO4) and evaporated in vacuo. The remaining residue was recrystallized from a mixture of iPr2O and heptane to give 1-[9-(1-carboxycyclobutyl)-5-oxononyl]-1-cyclo-butanecarboxylic acid (4.41 g, 56%) as small, white granules. mp 69-70° C. 1H NMR (CDCl3): δ=11.2 (br s, 2H), 2.50-2.37 (m, 4H), 2.39 (t, J=7.2 Hz, 4H), 1.96-1.84 (m, 8H), 1.81-1.75 (m, 4H), 1.57 (quintet, J=7.4 Hz, 4H), 1.26-1.12 (m, 4H). 13C NMR (CDCl3): δ=210.6, 183.4 (2×), 47.6 (2×), 42.7 (2×), 37.8 (2×), 30.1 (4×). 24.7 (2×), 24.1 (2×), 15.7 (2×). Anal. calcd for C19H30O5: C, 67.43; H, 8.93. found: C, 67.19; H, 8.97.

Workup

  1. temperatureat reflux temperature for 17 h
  2. concentrationconcentrated in vacuo to a smaller volume
  3. additionH2O (150 mL) was added
  4. extractionthe resulting mixture was extracted with Et2O (50 mL)
  5. extractionextracted with Et2O (1×100 mL, 2×50 mL)
  6. washwashed with brine (50 mL)
  7. dry with materialdried (Na2SO4)
  8. customevaporated in vacuo
  9. customThe remaining residue was recrystallized from a mixture of iPr2O and heptane

Sources & evidence

ORD record
ord-6e294ea1cba14bfa83821739a5e5299d
Source dataset
uspto-grants-2015_04
Patent number
US09006290B2

Reaction notes

Loading…