Hydrochloric Acid → HCID 57438721, compound

HRID 2354507Notes

Reaction equation

HRID 2354507 reaction equation
[CH3:1][C:2]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][N:10]=1)([CH3:7])[C:3]([O:5]C)=[O:4].O.[OH-].[Li+].Cl>O1CCCC1.O>[CH3:7][C:2]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][N:10]=1)([CH3:1])[C:3]([OH:5])=[O:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 57438722HCID 57438722, compound

Product 1

HCID 57438721HCID 57438721, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-methyl-2-(5-cyano-2-pyridyloxy)propionate (12 mg) in tetrahydrofuran (2 mL) and water (1 mL) was added lithium hydroxide monohydrate (10 mg). After stirring at room temperature overnight, the reaction mixture was acidified with 1 N hydrochloric acid, and the resulting mixture was partitioned between water (50 mL) and ethyl acetate (50 mL). The organic layer was separated, washed with water and brine, dried over sodium sulfate, filtered and concentrated to dryness to give the title compound. 1H NMR (500 MHz, CD3OD): δ 8.23 (d, 1H), 7.96 (dd, 1H), 6.91 (d, 1H), 1.64 (s, 6H).

Workup

  1. customthe resulting mixture was partitioned between water (50 mL) and ethyl acetate (50 mL)
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-d39b702d76a24bc1b21146de1b2193ad
Source dataset
uspto-grants-2010_07
Patent number
US07754188B2

Reaction notes

Loading…