Sodium hydride → HCID 67973797, compound

HRID 1844082Notes

Reaction equation

HRID 1844082 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:5]2.[H-].[Na+]>CN(C=O)C>[CH2:15]([O:14][C:12](=[O:13])[CH2:6][C:6]1([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=2)[C:7]1=[O:11])[CH3:16]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 10242642HCID 10242642, compound

Product 1

HCID 67973797HCID 67973797, compoundYield 133.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
65 °C

Procedure

A mixture of ethyl 5-fluoro-1-oxo-indane-2-carboxylate (1.4 g, 6.3 mmol), sodium hydride (278 mg, 6.9 mmol, 60% in mineral oil) and DMF (dry, 2.5 ml) was heated to 65° C. for one hour. A solution of bromo ethylester (1.15 g, 0.8 ml, 6.9 mmol) in dry DMF (4.0 ml) was added at the same temperature and heating was continued for additional 3 h. After complete the reaction, reaction mass was evaporated to dryness, 5 ml water was added and the suspension was extracted with ethyl acetate (25 ml×3). Combined organic layer was washed with brine, dried over sodium sulphate, evaporated and subjected to column chromatography using ethyl acetate/hexane (15%) to yield a desired product (1.3 g, 72%).

Workup

  1. temperatureheating
  2. customAfter complete the reaction, reaction mass
  3. customwas evaporated to dryness, 5 ml water
  4. additionwas added
  5. extractionthe suspension was extracted with ethyl acetate (25 ml×3)
  6. washCombined organic layer was washed with brine
  7. dry with materialdried over sodium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-26d02dabfe1d48d8819f377992505f80
Source dataset
uspto-grants-2015_02
Patent number
US08946280B2

Reaction notes

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