Sodium Hydroxide → HCID 68509953, compound

HRID 1880612Notes

Reaction equation

HRID 1880612 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[N:8]=[CH:7][C:6]([C:9]([CH3:16])=[CH:10][C:11]([O:13]CC)=[O:12])=[CH:5][CH:4]=1.[OH-].[Na+]>C1COCC1.CCO>[F:17][C:2]([F:1])([F:18])[C:3]1[N:8]=[CH:7][C:6]([C:9]([CH3:16])=[CH:10][C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68512759HCID 68512759, compound

Product 1

HCID 68509953HCID 68509953, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 3-(6-(trifluoromethyl)pyridin-3-yl)but-2-enoate (2.9 g, 11 mmol) in EtOH/THF 1/1 (34 mL) was added 1M NaOH (aq.) (34 mL). The resulting mixture was heated at 60° C. for 1 h after which the reaction mixture was allowed to cool to rt. The volatiles were evaporated and the remaining water phase neutralized with 1 M HCl(aq.). The title compound (2.4 g, 10 mmol, 91%), which precipitated as a white solid, was filtered off and dried under vacuum at 55° C. over night. This material was used directly in the next step, without further purification.

Workup

  1. temperatureto cool to rt
  2. customThe volatiles were evaporated

Sources & evidence

ORD record
ord-df60790f11314b76bd7fabeeda82d5a7
Source dataset
uspto-grants-2012_11
Patent number
US08318768B2

Reaction notes

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