Lithium Hydroxide → HCID 28830820, compound

HRID 1623654Notes

Reaction equation

HRID 1623654 reaction equation
[OH-].[Li+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]#[N:31])=[C:8]([CH:21]=1)[C:9]([O:11]CC1C=CC=CC=1C#N)=[O:10]>O.C1COCC1>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]#[N:31])=[C:8]([CH:21]=1)[C:9]([OH:11])=[O:10]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67107147HCID 67107147, compound

Product 1

HCID 28830820HCID 28830820, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

A solution of lithium hydroxide (328 mg, 7.83 mmol) in water (20 m) was added dropwise to a stirred solution of (2-cyanophenyl)methyl 5-bromo-2-{[(2-cyanophenyl)methyl]oxy}benzoate (may be prepared as described in Description 34; 350 mg, 0.78 mmol) in THF (20 ml) over 1 min. The reaction mixture was stirred at 20° C. for 18 h. The organic phase was evaporated and the aqueous phase (20 ml) was extracted with ethyl acetate (20 ml). The aqueous phase (20 ml) was adjusted to pH 2 with 2M hydrochloric acid (1 ml). The residual water phase was extracted with ethyl acetate (3×20 ml). The organic phase was then evaporated in vacuo to yield the title compound as a light yellow solid. 160 mg.

Workup

  1. customThe organic phase was evaporated
  2. extractionthe aqueous phase (20 ml) was extracted with ethyl acetate (20 ml)
  3. extractionThe residual water phase was extracted with ethyl acetate (3×20 ml)
  4. customThe organic phase was then evaporated in vacuo

Sources & evidence

ORD record
ord-66cd56493572458a90e6b96a6d63b38d
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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