Methanol → HCID 89581241, compound

HRID 1501150Notes

Reaction equation

HRID 1501150 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[O:7][CH:8]([C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=[O:15])=[CH:12][CH:11]=1)[CH3:9].O.[OH-].[Li+].O.CO>O1CCCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[O:7][CH:8]([C:10]1[CH:19]=[CH:18][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=1)[CH3:9]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 89580573HCID 89580573, compound

Product 1

HCID 89581241HCID 89581241, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of methyl 4-(1-(pyrimidin-2-yloxy)ethyl)benzoate (400 mg, 1.6 mmol), lithium hydroxide monohydrate (326 mg, 7.8 mmol), water (4 mL) and methanol (4 mL) in tetrahydrofuran (12 mL) was stirred at 20° C. for 5 hours. The reaction mixture was concentrated. The residue was acidified to pH=2 with concentrated hydrochloride solution. The mixture was extracted with ethyl acetate (20 mL×2). The organic phase was dried over sodium sulfate and filtered. The filtrate was concentrated. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=2:1) to give 4-(1-(pyrimidin-2-yloxy)ethyl)benzoic acid as a white solid (300 mg, 88%). LRMS (M+H+) m/z: 244.08. found 244.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionThe mixture was extracted with ethyl acetate (20 mL×2)
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=2:1)

Sources & evidence

ORD record
ord-458cfe2d0f3d480a9f733a8cca6a3f17
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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