Hydrochloric Acid → HCID 86672785, compound

HRID 1755065Notes

Reaction equation

HRID 1755065 reaction equation
O[Li].O.C([O:11][C:12]([CH:14]1[CH2:19][CH2:18][CH:17]([CH2:20][C:21]([F:27])([F:26])[C:22]([F:25])([F:24])[F:23])[CH2:16][CH2:15]1)=[O:13])C1C=CC=CC=1.Cl.CC(C)([O-])C.[K+]>C1COCC1.O>[F:26][C:21]([F:27])([C:22]([F:23])([F:25])[F:24])[CH2:20][CH:17]1[CH2:18][CH2:19][CH:14]([C:12]([OH:13])=[O:11])[CH2:15][CH2:16]1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 168937Lithium hydroxide, monohydrateHCID 23665647Potassium tert-butoxideHCID 86672783HCID 86672783, compound

Product 1

HCID 86672785HCID 86672785, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiOH.H2O (3.8 mg, 0.091 mmol) was added to a solution of 4-(2,2,3,3,3-pentafluoro-propyl)-cyclohexanecarboxylic acid benzyl ester (cis:trans=11:1) (11.4 mg, 0.0325 mmol) in THF (0.15 ml)-H2O (0.15 mL). The mixture was stirred at room temperature for 16 hours, and then adjusted to pH 2 with a 1 N aqueous HCl solution and extracted with dichloromethane. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The resulting residue was dissolved in tert-butanol (0.4 ml), and potassium tert-butoxide (10 mg, 0.089 mmol) was added. The mixture was stirred at room temperature for two hours, and then adjusted to pH 3 with a 1 N aqueous HCl solution and extracted with dichloromethane. The organic layer was then dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by column chromatography (hexane/ethyl acetate=5/1) to give 4-(2,2,3,3,3-pentafluoro-propyl)-cyclohexanecarboxylic acid (cis:trans=9:1) (8.5 mg, 100%).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe resulting residue was dissolved in tert-butanol (0.4 ml)
  5. stirringThe mixture was stirred at room temperature for two hours
  6. extractionextracted with dichloromethane
  7. dry with materialThe organic layer was then dried over MgSO4
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified by column chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-ab106d1f239c4d818234ad95e3842eb4
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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