Potassium Carbonate → Ethyl 2-(2-fluoroethyl)-5-methoxy-1-oxoindane-2-carboxylate

HRID 859243Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:6]2.C([O-])([O-])=O.[K+].[K+].Br[CH2:25][CH2:26][F:27]>CC(N(C)C)=O>[F:27][CH2:26][CH2:25][C:7]1([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:6][C:5]2[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:8]1=[O:12]

Participants

Conditions

Temperature: 65 °C

Procedure

To a mixture of ethyl 5-methoxy-1-oxoindane-2-carboxylate (crude product from the preceding two reactions, ˜190 mmol), K2CO3 (53.8 g, 389 mmol) and KI (64.7 g, 390 mmol) in anhydrous dimethylacetamide (792 mL) was added 1-bromo-2-fluoroethane (18.4 mL, 247 mmol) and the mixture was stirred and heated at 65° C. After 20 hours, analysis of an aliquot by NMR showed the reaction to be complete. After cooling to room temperature, most of the dimethylacetamide was removed by evaporation at reduced pressure. The residue was partitioned between EtOAc and water and the organic phase was washed with water (4 times) and brine and dried over Na2SO4. Filtration and removal of the solvent under reduced pressure gave crude ethyl 2-(2-fluoroethyl)-5-methoxy-1-oxoindane-2-carboxylate which was used in the next step without purification.

Workup

customthe reaction
customwas removed by evaporation at reduced pressure
customThe residue was partitioned between EtOAc and water
washthe organic phase was washed with water (4 times) and brine
dry with materialdried over Na2SO4
filtrationFiltration and removal of the solvent under reduced pressure

Sources & evidence

ORD record: ord-2b2bb60d002a4136a34f1ac72f33e75f
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07151196B2

Reaction notes

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