Lithium Hydroxide → HCID 86279504, compound

HRID 2170736Notes

Reaction equation

HRID 2170736 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:34])[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]2[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)[C:14]2=[O:33])=[CH:8][CH:7]=1>C1COCC1>[O:33]=[C:14]1[C:15]2[C:20](=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:30])([F:31])[F:32])[CH:24]=3)[CH:18]=[CH:17][CH:16]=2)[CH2:21][CH2:22][CH:13]1[CH2:12][C:9]1[CH:8]=[CH:7][C:6]([C:5]([OH:34])=[O:4])=[CH:11][CH:10]=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 methyl4-((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-b9324216aaf84ae4b39c997048951fa5
Source dataset
uspto-grants-2015_06
Patent number
US09051294B2

Reaction notes

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