Methyl iodide → Ethyl 1-methyl-2-oxocyclopentane-1-carboxylate

HRID 530235ノート

反応式

HRID 530235 の反応式
[C:1](=O)([O-])[O-].[K+].[K+].[O:7]=[C:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]([O:15][CH2:16][CH3:17])=[O:14].CI>CC(C)=O>[CH3:1][C:9]1([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:10][CH2:11][CH2:12][C:8]1=[O:7]

参加物

5

反応物 3

HCID 6328Methyl iodide2 回HCID 11430Potassium CarbonateHCID 69136Ethyl 2-oxocyclopentanecarboxylate

生成物 1

HCID 227353Ethyl 1-methyl-2-oxocyclopentane-1-carboxylate収率 82%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a stirred suspension of dry potassium carbonate (16.64 g, 120.4 mmol) in dry acetone (200 mL) under argon was added ethyl 2-oxocyclopentanecarboxylate (9.40 g, 60.2 mmol) followed by methyl iodide (7.5 mL, 120.4 mmol). The reaction was heated to reflux for 3 hours and then another portion of methyl iodide (7.5 mL, 120.4 mmol) was added and the reaction was refluxed overnight. The reaction mixture was cooled and then filtered through a silica gel pad and the solid was washed with acetone (100 mL×3). The organic phase was concentrated under reduced pressure and the residue dispersed in acetone (200 mL) and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate=100/1->50/1) to afford the title compound as a colorless liquid (8.35 g, Yield: 82%). 1H NMR (400 MHz, CDCl3) δ 4.22-4.10 (m, 2H), 2.57-2.40 (m, 2H), 2.36-2.27 (m, 1H), 2.11-2.00 (m, 1H), 1.98-1.83 (m, 2H), 1.31 (s, 3H), 1.25 (t, J=7.0 Hz, 3H) ppm.

後処理

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 3 hours
  3. temperaturethe reaction was refluxed overnight
  4. temperatureThe reaction mixture was cooled
  5. filtrationfiltered through a silica gel pad
  6. washthe solid was washed with acetone (100 mL×3)
  7. concentrationThe organic phase was concentrated under reduced pressure
  8. additionthe residue dispersed in acetone (200 mL)
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. customthe residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate=100/1->50/1)

出典と根拠

ORDレコード
ord-962d8357b66f4a4482aa69baca161838
出典データセット
uspto-grants-2016_05
特許番号
US09353063B2

反応ノート

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