Lithium Hydroxide → HCID 28830798, compound

HRID 1623644Notes

Reaction equation

HRID 1623644 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][C:27]([C:30]#[N:31])=[CH:26][CH:25]=2)=[C:8]([CH:21]=1)[C:9]([O:11]CC1C=CC(C#N)=CC=1)=[O:10]>O.C1COCC1>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([C:30]#[N:31])=[CH:28][CH:29]=2)=[C:8]([CH:21]=1)[C:9]([OH:11])=[O:10]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67107238HCID 67107238, compound

Product 1

HCID 28830798HCID 28830798, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

Lithium hydroxide (281 mg, 6.71 mmol) in water (20 ml) was added dropwise to a stirred solution of (4-cyanophenyl)methyl 5-bromo-2-{[(4-cyanophenyl)methyl]oxy}benzoate (may be prepared as described in Description 23; 300 mg, 0.67 mmol) in THF (20 ml) over 5 min. The reaction mixture was stirred at 20° C. for 16 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 aqueous phase was then 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. 145 mg.

Workup

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

Sources & evidence

ORD record
ord-d4135beab963425d98e6faa2c95375e5
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

Loading…