Lithium Hydroxide → HCID 59191230, compound

HRID 626010Notes

Reaction equation

HRID 626010 reaction equation
[OH:1][C:2]1[CH:15]=[C:14]([CH2:16][CH2:17][CH3:18])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8](O)=[N:9][CH:10]=1.[Li+].[OH-].[CH2:21](Br)[CH3:22].[C:24]([O-:27])(O)=O.[Na+].[CH3:29]N(C=O)C>>[CH2:21]([O:1][C:2]1[CH:15]=[C:14]([CH2:16][CH2:17][CH3:18])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:6]=[CH:29][C:24](=[O:27])[N:9]([CH2:8][CH3:7])[CH:10]=1)[CH3:22]

Participants

6

Reactant 5

HCID 3939Lithium HydroxideHCID 6228DimethylformamideHCID 6332Ethyl BromideHCID 516892Sodium BicarbonateHCID 178439263HCID 178439263, compound

Product 1

HCID 59191230HCID 59191230, compoundYield 58%

Procedure

To a solution of 5-(2-hydroxy-4-propylphenoxy)pyridin-2-ol (0.08 mmol; 20 mg) under argon, in anhydrous DMF (0.5 mL) cooled to 0° C., were added LiOH (0.09 mmol; 2 mg), then EtBr (0.09 mmol; 0.007 mL). After allowing the mixture to warm overnight up to room temperature, the reaction was neutralised with NaHCO3 (1 mL), extracted with ethyl acetate (3*3 mL). Combined organic phases were washed with water (3 mL), dried over MgSO4, concentrated in vacuo to yield the title compound as a brown oil (14 mg; 0.05 mmol; 58%), used as such.

Workup

  1. temperatureto warm overnight up to room temperature
  2. extractionextracted with ethyl acetate (3*3 mL)
  3. washCombined organic phases were washed with water (3 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5529fe8b07f745b4ad8a228f0a71dca4
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Reaction notes

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