Sulfuric Acid → HCID 58188147, compound

HRID 1845293Notes

Reaction equation

HRID 1845293 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][N:15]=2)[CH:13]=1)[C:7]([O:9]C)=[O:8].[OH-].[Li+].OS(O)(=O)=O>O1CCOCC1.O>[CH3:1][O:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][N:15]=2)[CH:13]=1)[C:7]([OH:9])=[O:8]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 3939Lithium HydroxideHCID 58188125HCID 58188125, compound

Product 1

HCID 58188147HCID 58188147, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of methyl 3-(methoxymethyl)-5-(5-methylpyridin-2-yl)benzoate (75 mg, 0.28 mmol) in 1,4-dioxane (3 mL) and water (0.3 mL) was added lithium hydroxide (66 mg, 2.8 mmol) and the reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was acidified with 2N aq. H2SO4 to pH=7-8, and then extracted with EtOAc (20 mL×3). The combined organic layers were washed with brine, dried (MgSO4), and concentrated to afford the title compound. 1H NMR (D2O, 400 MHz): 8.10 (s, 1H), 7.98 (s, 1H), 7.72 (s, 1H), 7.51 (s, 1H), 7.40 (d, J=8.0 Hz, 1H), 7.32 (d, J=8.4 Hz, 1H), 4.41 (s, 2H), 3.32 (s, 3H), 2.13 (s, 3H).

Workup

  1. extractionextracted with EtOAc (20 mL×3)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-68d96951b0d44e2caf742d26eb0b96a2
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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