Water → HCID 59138622, compound

HRID 1670730Notes

Reaction equation

HRID 1670730 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]([CH3:15])([CH3:14])[C:10]([O:12]C)=[O:11])=[CH:4][CH:3]=1.O.[OH-].[Li+].O>O1CCOCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:9]([CH3:15])([CH3:14])[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 59138592HCID 59138592, compound

Product 1

HCID 59138622HCID 59138622, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of methyl 3-(6-chloropyridin-3-yl)-2,2-dimethyl-3-phenylpropanoate (Example 4(c), 67 mg, 0.22 mmol), lithium hydroxide monohydrate (55 mg, 1.3 mmol), water (2 mL), and dioxane (2 mL) was stirred at 110° C. for 1.5 hr and then concentrated. The residue was partitioned between water (4 mL) and diethyl ether (6 mL) were added. The ether layer was reextracted with water (1 mL). The combined aqueous solutions were neutralized with aqueous 10% citric acid solution to pH=5 and extracted with ethyl acetate (3×5 mL). The combined ethyl acetate extracts were washed with brine (2 mL), dried (Na2SO4) and concentrated to give 3-(6-chloropyridin-3-yl)-2,2-dimethyl-3-phenylpropanoic acid (57 mg, 0.20 mmol, 89% yield). MS found: (M−H)−=288.19.

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between water (4 mL) and diethyl ether (6 mL)
  3. additionwere added
  4. extractionextracted with ethyl acetate (3×5 mL)
  5. washThe combined ethyl acetate extracts were washed with brine (2 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5a12279583064422ba2e1f0ae71aac12
Source dataset
uspto-grants-2011_08
Patent number
US07994190B2

Reaction notes

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