Potassium Hydroxide → HCID 11304084, compound

HRID 873276Notes

Reaction equation

HRID 873276 reaction equation
C([O:3][C:4](=[O:32])[C:5]([CH3:31])([CH3:30])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13](=[O:29])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([CH3:28])([CH3:27])[C:22]([O:24]CC)=[O:23])C.[OH-].[K+]>CCO.O>[CH3:30][C:5]([CH3:31])([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13](=[O:29])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([CH3:28])([CH3:27])[C:22]([OH:24])=[O:23])[C:4]([OH:32])=[O:3]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 11476562HCID 11476562, compound

Product 1

HCID 11304084HCID 11304084, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 209j (11.63 g, 25.6 mmol) in EtOH and H2O (3:1, 200 mL) was added powdered KOH (85%, 4.31 g, 65.3 mmol). The resulting mixture was refluxed for 19 h and concentrated in vacuo until all of the EtOH was removed. Water (200 mL) was added and the resulting mixture was extracted with Et2O (2×200 mL). The aqueous phase was acidified with aqueous HCl (4 M) to pH ˜1 and extracted with Et2O (3×200 mL). The combined Et2O layers of the latter extraction were dried over anhydrous Na2SO4 and evaporated in vacuo. The remaining white solid was recrystallized from heptane/iPr2O to give 210j (7.56 g, 74%) as white crystals. Mp 74.3-77.3° C. 1H NMR (CD3OD): δ (ppm): 2.43 (t, J=7.3, 4 H), 1.57-1.50 (m, 8H), 1.33-1.21 (m, 16H), 1.14 (s, 12H). 13C NMR (CD3OD): δ (ppm): 214.5, 182.1, 43.6, 43.2, 42.0, 31.2, 30.4, 30.38, 26.2, 25.9, 25.0. HRMS: Calcd for C23H42O5 (M+): 398.3028, found: 398.3032.

Workup

  1. temperatureThe resulting mixture was refluxed for 19 h
  2. concentrationconcentrated in vacuo until all of the EtOH
  3. customwas removed
  4. additionWater (200 mL) was added
  5. extractionthe resulting mixture was extracted with Et2O (2×200 mL)
  6. extractionextracted with Et2O (3×200 mL)
  7. extractionThe combined Et2O layers of the latter extraction
  8. dry with materialwere dried over anhydrous Na2SO4
  9. customevaporated in vacuo
  10. customThe remaining white solid was recrystallized from heptane/iPr2O

Sources & evidence

ORD record
ord-5311189b7d9048e4929dac774a6dc6d5
Source dataset
uspto-grants-2015_03
Patent number
US08975300B2

Reaction notes

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