Lithium Hydroxide → HCID 28881383, compound

HRID 1623646Notes

Reaction equation

HRID 1623646 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]=[C:26]([C:30]#[N:31])[CH:25]=2)=[C:8]([CH:21]=1)[C:9]([O:11]CC1C=CC=C(C#N)C=1)=[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]=[C:26]([C:30]#[N:31])[CH:25]=2)=[C:8]([CH:21]=1)[C:9]([OH:11])=[O:10]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67107390HCID 67107390, compound

Product 1

HCID 28881383HCID 28881383, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

A solution of lithium hydroxide (386 mg, 9.19 mmol) in water (20.00 mL) was added dropwise to a stirred solution of (3-cyanophenyl)methyl 5-bromo-2-{[(3-cyanophenyl)methyl]oxy}benzoate (may be prepared as described in Description 25; 411 mg, 0.92 mmol) in THF (20 ml) over 1 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 by 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 evaporated in vacuo to yield the title compound as an off-white solid. 200 mg.

Workup

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

Sources & evidence

ORD record
ord-b65340e4bb7d4507b35a54310c30fbfe
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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