Cyclobutanol → 3-Cyclobutoxypyridine-2-carboxylic acid

HRID 341565Notes

Reaction equation

HRID 341565 reaction equation
CC(C)([O-])C.[K+].F[C:8]1[C:9]([C:14]([OH:16])=[O:15])=[N:10][CH:11]=[CH:12][CH:13]=1.[CH:17]1([OH:21])[CH2:20][CH2:19][CH2:18]1>>[CH:17]1([O:21][C:8]2[C:9]([C:14]([OH:16])=[O:15])=[N:10][CH:11]=[CH:12][CH:13]=2)[CH2:20][CH2:19][CH2:18]1

Participants

4

Reactant 3

HCID 76218CyclobutanolHCID 27627863-Fluoropyridine-2-carboxylic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 668030753-Cyclobutoxypyridine-2-carboxylic acidYield 100%

Procedure

Potassium tert-butoxide (358 mg, 3.19 mmol) was suspended in cyclobutanol (0.5 mL), 3-fluoropyridine-2-carboxylic acid (150 mg, 1.06 mmol) was added and the reaction was stirred at 100 C for 18 h. The mixture was evaporated under vacuum to afford the title compound (100% conversion assumed), which was used in the next step without further purification. Method C HPLC-MS: MH+ requires m/z=194. Found: m/z=194, Rt=0.83 min (100%).

Workup

  1. customThe mixture was evaporated under vacuum

Sources & evidence

ORD record
ord-e1e77a318d52448f95826b6dc7321024
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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