Dimethylformamide → HCID 20069405, compound

HRID 982208Notes

Reaction equation

[Na+].[OH:2][CH:3]([CH2:7][CH3:8])[C:4]([O-:6])=[O:5].CN(C)C=O.[H-].[Na+].Cl[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[N:18]=1>C(Cl)(Cl)Cl.O>[F:24][C:23]([F:26])([F:25])[C:19]1[N:18]=[C:17]([O:2][CH:3]([CH2:7][CH3:8])[C:4]([OH:6])=[O:5])[CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 105 °C

Procedure

2-hydroxybutyric acid sodium salt (10 g) was added to dry dimethylformamide (100 ml) and oil free sodium hydride (2 g) added in a single portion with stirring under nitrogen. The reaction mixture was stirred at ambient temperature for 30 minutes and then at about 80° C. for 10 minutes prior to addition of 2-chloro-6-trifluoromethylpyridine (10 g). The reaction mixture was then heated to 100-110° C. for 1 hour. The mixture was poured into an equal volume mixture of water and chloroform (1 liter) and the original layer made just acidic (pH4), followed by vigorous extraction into the organic phase which was separated, washed and dried. Chromatography gave a colorless solid which was recrystallized from hexane to give colorless crystals mp. 118° C. (11.9 g) of 2-(6-trifluoromethyl-2-pyridinyloxy)butyric acid.

Workup

additionadded in a single portion
stirringThe reaction mixture was stirred at ambient temperature for 30 minutes
extractionfollowed by vigorous extraction into the organic phase which
customwas separated
washwashed
customdried
customChromatography gave a colorless solid which
customwas recrystallized from hexane

Sources & evidence

ORD record: ord-a5435f5fe19d4d14bbc4a201f2a19338
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04994616

Reaction notes

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