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

HRID 362809Notes

Reaction equation

HRID 362809 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-fc83ea7dabaa4212b5d1ae7ca9cc4b26
Source dataset
uspto-grants-1999_02
Patent number
US05872118

Reaction notes

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