Hydrochloric Acid → HCID 68006818, compound

HRID 1475649Notes

Reaction equation

HRID 1475649 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[C:9]([O:11]C)=[O:10])=[C:4]([F:18])[CH:3]=1.CO.[OH-].[Na+].Cl>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17]2)[C:9]([OH:11])=[O:10])=[C:4]([F:18])[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 68170291HCID 68170291, compound

Product 1

HCID 68006818HCID 68006818, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

7.55 g (27.9 mmol) of methyl (4-chloro-2-fluorophenyl)(cyclopentyl)acetate were dissolved in 32 ml each of THF, methanol and water, and 11.15 g (287.9 mmol) of sodium hydroxide were added with ice cooling. The reaction mixture was stirred at RT overnight and then diluted with water and adjusted to pH 2 with 1 N hydrochloric acid. The aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated under reduced pressure. The solid that remained was triturated with water, filtered off with suction and dried thoroughly under reduced pressure. This gave 6.96 g of the target compound (97.2% of theory).

Workup

  1. extractionThe aqueous phase was extracted three times with ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe solid that remained was triturated with water
  5. filtrationfiltered off with suction
  6. customdried thoroughly under reduced pressure

Sources & evidence

ORD record
ord-3847145e906242bc9c6162bedd52b57f
Source dataset
uspto-grants-2015_04
Patent number
US09018258B2

Reaction notes

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