1,2-Dimethoxyethane → HCID 23293595, compound

HRID 362864Notes

Reaction equation

HRID 362864 reaction equation
Br[CH:2]1[C:10]2[C:5](=[CH:6][C:7]([F:11])=[CH:8][CH:9]=2)[C:4](=[O:12])[CH2:3]1.C(COC)[O:14]C>O.C(=O)([O-])[O-].[Ag+2]>[OH:14][CH:2]1[C:10]2[C:5](=[CH:6][C:7]([F:11])=[CH:8][CH:9]=2)[C:4](=[O:12])[CH2:3]1

Participants

5

Reactant 2

HCID 80711,2-DimethoxyethaneHCID 232936813-Bromo-6-fluoro-1-indanone

Product 1

HCID 23293595HCID 23293595, compound

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 962WaterSolvent

Procedure

A mixture of 3-bromo-6-fluoro-1-indanone (2.50 g, 10.0 mmoles) and silver carbonate (4.19 g, 15.2 mmoles, Aldrich) in dimethoxyethane (85 mL) and water (65 mL) was stirred overnight at ambient temperature. The mixture was filtered through a pad of celite, and the filtrate was diluted with water (500 mL) and extracted with ethyl acetate (4×100 mL). The combined extracts were washed with water (100 mL) and brine (75 mL), dried over sodium sulfate, filtered, and evaporated in vacuo to give 2.80 g (quantitative) of crude 3-hydroxy-6-fluoro-1-indanone which was used without further purification. Chromatography of 0.41 g on silica gel, eluting with hexane: ethyl acetate (3:4) gave 0.050 g of analytically pure 3-hydroxy-6-fluoro-1-indanone as a tan solid, mp 73°-76° C.;

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. additionthe filtrate was diluted with water (500 mL)
  3. extractionextracted with ethyl acetate (4×100 mL)
  4. washThe combined extracts were washed with water (100 mL) and brine (75 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-d1d46d2ed5a84565a4b8ded541278783
Source dataset
uspto-grants-1999_02
Patent number
US05872118

Reaction notes

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