Lithium Hydroxide → Lithium 2-(6-fluoro-1-hydroxy-1-indanyl)acetate

HRID 1954856Notes

Reaction equation

HRID 1954856 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2([CH2:12][C:13]([O:15]CC)=[O:14])[OH:11])=[CH:4][CH:3]=1.[OH-].[Li+:19]>C(O)C>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2([CH2:12][C:13]([O-:15])=[O:14])[OH:11])=[CH:4][CH:3]=1.[Li+:19]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 23293626Ethyl 2-(6-fluoro-1-hydroxy-1-indanyl)acetate

Product 1

HCID 23678141Lithium 2-(6-fluoro-1-hydroxy-1-indanyl)acetateYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 2-(6-fluoro-1-hydroxy-1-indanyl)acetate (2.0 g, 8.4 mmol), 1N lithium hydroxide (8.4 mL) and absolute ethanol (13.0 mL) was stirred for 18 h at room temperature. The mixture was concentrated in vacuo, diluted with H2O and extracted with diethyl ether. The aqueous phase was concentrated in vacuo, diluted with toluene (100 mL) and concentrated in vacuo to give lithium 2-(6-fluoro-1-hydroxy-1-indanyl)acetate as a white solid (1.4 g, 77%);

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additiondiluted with H2O
  3. extractionextracted with diethyl ether
  4. concentrationThe aqueous phase was concentrated in vacuo
  5. additiondiluted with toluene (100 mL)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b93e35118e074d19b685b745d5f0956f
Source dataset
uspto-grants-2000_09
Patent number
US06124284

Reaction notes

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