Methyl iodide → 5183-61-9

HRID 1371574ノート

反応式

HRID 1371574 の反応式
[H-].[Na+].[O:3]=[C:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]1[C:10]([O:12][CH2:13][CH3:14])=[O:11].[CH2:15]([Li])CCC.IC>O1CCCC1>[CH3:15][CH:9]1[CH2:8][CH2:7][CH2:6][CH:5]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:4]1=[O:3]

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 95543Ethyl 2-oxocyclohexanecarboxylateHCID 178418339Butyllithium

生成物 1

HCID 123681345183-61-9

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
5 °C

実験手順

To a suspension of sodium hydride (5.0 g, 0.125 mol) in tetrahydrofuran (250 mL) was added a solution of ethyl 2-oxocyclohexanecarboxylate (19.9 mL, 0.125 mol) in tetrahydrofuran (30 mL) whilst maintaining the temperature of the mixture between 10° C. and 15° C. by means of an ice bath. After stirring at 5° C. for 1 hour, butyl lithium (52.5 mL, 2.5 M solution in hexanes, 131 mmol) was added dropwise while maintaining the temperature below 12° C. After stirring at 5° C. for 30 minutes, iodomethane (7.8 mL, 125 mmol) was added. The reaction mixture was stirred at 5° C. for 1.5 hours and then quenched with a saturated solution of ammonium chloride. The mixture was diluted with ethyl ether, washed with water. The organic extracts were dried over magnesium sulfate and concentrated. The resulting residue was distilled (100–110° C., 0.1 torr) to obtain the title compound as a colorless oil.

後処理

  1. temperaturewhilst maintaining the temperature of the mixture between 10° C. and 15° C. by means of an ice bath
  2. temperaturewhile maintaining the temperature below 12° C
  3. stirringAfter stirring at 5° C. for 30 minutes
  4. stirringThe reaction mixture was stirred at 5° C. for 1.5 hours
  5. customquenched with a saturated solution of ammonium chloride
  6. additionThe mixture was diluted with ethyl ether
  7. washwashed with water
  8. dry with materialThe organic extracts were dried over magnesium sulfate
  9. concentrationconcentrated
  10. distillationThe resulting residue was distilled (100–110° C., 0.1 torr)

出典と根拠

ORDレコード
ord-2afc76b8c8a04ac2b47c2c5bd71a3bee
出典データセット
uspto-grants-2007_01
特許番号
US07157475B2

反応ノート

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