Lithium Hydroxide → HCID 86279504, compound

HRID 1482447Notes

Reaction equation

HRID 1482447 reaction equation
[OH-].[Li+].[O:3]=[C:4]1[C:13]2[C:8](=[C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=3)[CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][CH:5]1[CH2:24][C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31]C)=[O:30])=[CH:27][CH:26]=1>C1COCC1>[O:3]=[C:4]1[C:13]2[C:8](=[C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:21])([F:22])[F:23])[CH:15]=3)[CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][CH:5]1[CH2:24][C:25]1[CH:26]=[CH:27][C:28]([C:29]([OH:31])=[O:30])=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 117665522HCID 117665522, compound

Product 1

HCID 86279504HCID 86279504, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Aqueous lithium hydroxide (1 N, 0.11 mL, 0.11 mmol) was added to a solution of methyl 4-((1-oxo-5-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydronaphthalen-2-yl)methyl)benzoate (10 mg, 0.023 mmol) in THF (0.23 mL) in a 1 dram vial. The vial was sealed and heated at 40° C. After 24 h, the reaction mixture was allowed to cool and the volatiles were evaporated under a stream of nitrogen. The residue was diluted with water (0.5 mL), acidified with 1 N aqueous HCl (0.5 mL) and extracted with EtOAc (3×2 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo to afford 9 mg of the title compound.

Workup

  1. customThe vial was sealed
  2. temperatureto cool
  3. customthe volatiles were evaporated under a stream of nitrogen
  4. additionThe residue was diluted with water (0.5 mL)
  5. extractionextracted with EtOAc (3×2 mL)
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c39c759a001f4af9a20cfa8ced4cb56c
Source dataset
uspto-grants-2016_08
Patent number
US09415027B2

Reaction notes

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