Hydrochloric Acid → HCID 66817213, compound

HRID 1755041Notes

Reaction equation

HRID 1755041 reaction equation
[OH-].[Na+].C([O:10][C:11]([CH:13]1[CH2:18][CH2:17][CH:16]([CH2:19][CH:20]=[C:21]([F:23])[F:22])[CH2:15][CH2:14]1)=[O:12])C1C=CC=CC=1.Cl.O[Li].O>CO.C1COCC1.O>[F:22][C:21]([F:23])=[CH:20][CH2:19][CH:16]1[CH2:17][CH2:18][CH:13]([C:11]([OH:12])=[O:10])[CH2:14][CH2:15]1

Participants

8

Reactant 4

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 168937Lithium hydroxide, monohydrateHCID 66817873HCID 66817873, compound

Product 1

HCID 66817213HCID 66817213, compoundYield 85,028.602%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 1 N aqueous NaOH solution (0.084 ml, 0.084 mmol) was added to a solution of 4-(3,3-difluoro-allyl)-cyclohexanecarboxylic acid benzyl ester (trans:cis=4:1) (14.1 mg, 0.0478 mmol) in methanol (1.0 mL). The mixture was stirred at room temperature for 1.5 hours, and then adjusted to pH 6 with a 1 N aqueous HCl solution and concentrated under reduced pressure. The resulting residue was adjusted to pH 3 with dilute hydrochloric acid and extracted with dichloromethane, and the organic layer was dried over MgSO4 and concentrated under reduced pressure. The resulting residue was dissolved in THF (0.2 ml)-H2O (0.2 ml), and LiOH.H2O (7.7 mg, 0.18 mmol) was added. The mixture was stirred at room temperature for three 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) to give 4-(3,3-difluoro-allyl)-cyclohexanecarboxylic acid (8.3 g, 86%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionextracted with dichloromethane
  3. dry with materialthe organic layer was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. additionwas added
  6. stirringThe mixture was stirred at room temperature for three hours
  7. extractionextracted with dichloromethane
  8. dry with materialThe organic layer was then dried over MgSO4
  9. concentrationconcentrated under reduced pressure
  10. customThe resulting residue was purified by column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-90a7b25e76c24cec9985df0b298f9b43
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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