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

HRID 862758Notes

Reaction equation

HRID 862758 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 18h 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%); NMR (DMSO-d6): d 8.90 (s, 1H, OH), 6.88-7.18 (m, 3H, Ar), 2.55-2.83 (m, 2H, ArCH2), 2.13 (s, 2H, CH2CO), 1.88-2.07 (m, 2H, CH2).

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-8bc6170b64e34a44ab88a6b04c1035dc
Source dataset
uspto-grants-1998_02
Patent number
US05719186

Reaction notes

Loading…