Hydrochloric Acid → 3-(6-(trifluoromethyl)pyridin-3-yl)propanoic Acid

HRID 2358012Notes

Reaction equation

HRID 2358012 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:19])[CH2:7][CH2:8][C:9]1[CH:10]=[N:11][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:14]=1.C(Cl)Cl.Cl>C1COCC1.O>[F:17][C:15]([F:16])([F:18])[C:12]1[N:11]=[CH:10][C:9]([CH2:8][CH2:7][C:6]([OH:19])=[O:5])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 168937Lithium hydroxide, monohydrateHCID 53406715Methyl 3-(6-(trifluoromethyl)pyridin-3-yl)propanoate

Product 1

HCID 27833903-(6-(trifluoromethyl)pyridin-3-yl)propanoic Acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (330 mg) is added in one portion to a solution of 3-(6-trifluoromethyl-pyridin-3-yl)-propionic acid methyl ester (610 mg) in a mixture of THF (15 mL) and water (5 mL). The mixture is stirred for 20 h at RT. DCM and aqueous HCl (1.0 M) are added, the layers are separated and the aqueous layer is extracted twice with DCM. The combined organic extracts are dried over MgSO4 and concentrated in vacuo to give the desired propionic acid as a beige solid.

Workup

  1. customthe layers are separated
  2. extractionthe aqueous layer is extracted twice with DCM
  3. dry with materialThe combined organic extracts are dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-951c9cd9b2d2478792fc3bc66a28d8fd
Source dataset
uspto-grants-2010_07
Patent number
US07763638B2

Reaction notes

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