Lithium Hydroxide → HCID 22312220, compound

HRID 1264666Notes

Reaction equation

HRID 1264666 reaction equation
[N:1]([CH:4]([C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[C:11]([F:16])[CH:10]=1)[C:5]([O:7]C)=[O:6])=[N+:2]=[N-:3].[OH-].[Li+]>C1COCC1.O>[N:1]([CH:4]([C:9]1[CH:10]=[C:11]([F:16])[CH:12]=[C:13]([F:15])[CH:14]=1)[C:5]([OH:7])=[O:6])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 22312564HCID 22312564, compound

Product 1

HCID 22312220HCID 22312220, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of methyl 2-azido-2-(3,5-difluorophenyl)acetate in THF/H2O (2.6:1) cooled to 0° C. was added 1.7 eq. of lithium hydroxide. The reaction mixture was stirred at room temperature for 3 hours and then poured into a separatory funnel. The mixture was extracted into water and washed with ether. The aqueous layer was acidified with 1N HCl and extracted with ethyl acetate. The organic layer was then washed with water and brine. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give 2-azido-2-(3,5-difluorophenyl)acetic acid.

Workup

  1. additionpoured into a separatory funnel
  2. extractionThe mixture was extracted into water
  3. washwashed with ether
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was then washed with water and brine
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d72316c570384c5394c88a60e30092b6
Source dataset
uspto-grants-2003_04
Patent number
US06544978B2

Reaction notes

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