Lithium hydroxide, monohydrate → HCID 59170417, compound

HRID 1445918Notes

Reaction equation

HRID 1445918 reaction equation
C[O:2][C:3](=[O:28])[C:4]([O:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[C:14]([CH3:27])[N:15]2[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([Br:9])[C:5]([F:8])([F:7])[F:6].O.[OH-].[Li+]>C1COCC1.O>[CH2:20]([N:15]1[C:16]2[C:12](=[C:11]([O:10][C:4]([Br:9])([C:5]([F:6])([F:7])[F:8])[C:3]([OH:28])=[O:2])[CH:19]=[CH:18][CH:17]=2)[CH:13]=[C:14]1[CH3:27])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59170414HCID 59170414, compound

Product 1

HCID 59170417HCID 59170417, compound

Reagents, catalysts & solvents 1

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

Procedure

To a solution of 2-(1-benzyl-2-methyl-1H-indol-4-yloxy)-2-bromo-3,3,3-trifluoro-propionic acid methyl ester (4) (0.07 g, 0.177 mmole) in THF:H2O (4:1, 10 mL), lithium hydroxide mono hydrate (0.01 g, 0.238 mmole) was added. The mixture was stirred at room temperature for 30 minutes. THF was evaporated and the mixture was acidified with 2M HCl to pH 3. The aqueous layer was extracted with ethyl acetate (3×10 mL). The organic layer was separated, dried over magnesium sulphate and concentrated to afford intermediate (5) as a pink solid. Yield: (0.066 g, 97%).

Workup

  1. customTHF was evaporated
  2. extractionThe aqueous layer was extracted with ethyl acetate (3×10 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5b9a29d96bde4e16bbc7d63d5d691154
Source dataset
uspto-grants-2010_02
Patent number
US07666898B2

Reaction notes

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