Tetrahydrofurfuryl alcohol → 6-((Tetrahydrofuran-2-yl)methoxy)-5-(trifluoromethyl)picolinic acid

HRID 624866

Reaction equation

Cl[C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[O:15]1[CH2:19][CH2:18][CH2:17][CH:16]1[CH2:20][OH:21].[OH-].[K+]>>[O:15]1[CH2:19][CH2:18][CH2:17][CH:16]1[CH2:20][O:21][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12]

Participants

Reactant 3

HCID 7360Tetrahydrofurfuryl alcohol

HCID 14797Potassium Hydroxide

HCID 707010166-Chloro-5-(trifluoromethyl)picolinic acid

Product 1

HCID 710876466-((Tetrahydrofuran-2-yl)methoxy)-5-(trifluoromethyl)picolinic acid

Procedure

In analogy to the procedure described in Example 4 a), 6-chloro-5-(trifluoromethyl)picolinic acid (CAN 855915-21-8) was reacted with (tetrahydrofuran-2-yl)methanol (CAN 97-99-4) in the presence of potassium hydroxide to yield the title compound as yellow solid; MS (EI): m/e=290.0 [MH+].

Sources & evidence

ORD record: ord-36267bffa0e54c9aab12d608f074bb6f
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303012B2

Linked notes

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