Lithium Hydroxide → HCID 89581384, compound

HRID 1501111Notes

Reaction equation

HRID 1501111 reaction equation
[O:1]([CH:8]([C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=[O:15])=[CH:12][N:11]=1)[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+]>O1CCCC1.CO.O>[O:1]([CH:8]([C:10]1[CH:19]=[CH:18][C:13]([C:14]([OH:16])=[O:15])=[CH:12][N:11]=1)[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 89580533HCID 89580533, compound

Product 1

HCID 89581384HCID 89581384, compoundYield 92.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 6-(1-phenoxyethyl)nicotinate (400 mg, 1.55 mmol) in tetrahydrofuran (12 mL), methanol (4 mL) and water (4 mL) was added lithium hydroxide (377 mg, 15.7 mmol). The resultant reaction mixture was stirred at room temperature for 2 hours. The solution was concentrated under reduced pressure and was treated with aqueous 1N hydrochloric acid (5 mL). Then the mixture was concentrated and the residue was purified by prep-thin layer chromatography to give 6-(1-phenoxyethyl)nicotinic acid (350 mg, 92.5%) as a white solid. LRMS (M+H+) m/z: calcd 244.09. found 244 1H NMR (300 MHz, DMSO) δ 9.08 (d, J=2.1 Hz, 1H), 8.32 (dd, J=8.1 Hz, J2=2.1 Hz, 1H), 7.60 (d, J=8.1 Hz, 1H), 7.19 (m, 2H), 6.87 (m, 3H), 5.49 (s, 1H), 1.66 (d, J=6.6 Hz, 3H).

Workup

  1. customThe resultant reaction mixture
  2. concentrationThe solution was concentrated under reduced pressure
  3. additionwas treated with aqueous 1N hydrochloric acid (5 mL)
  4. concentrationThen the mixture was concentrated
  5. customthe residue was purified by prep-thin layer chromatography

Sources & evidence

ORD record
ord-26fcc27cde1e4046893250a2c5e11bd4
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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