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

HRID 859243ノート

反応式

HRID 859243 の反応式
[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]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 129822-Fluoroethyl bromideHCID 12177975ethyl 5-methoxy-1-oxo-2,3-dihydro-1H-indene-2-carboxylate

生成物 1

HCID 16726730Ethyl 2-(2-fluoroethyl)-5-methoxy-1-oxoindane-2-carboxylate

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒2 回

反応条件

温度
65 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-2b2bb60d002a4136a34f1ac72f33e75f
出典データセット
uspto-grants-2006_12
特許番号
US07151196B2

反応ノート

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