Methyl iodide → Methyl 9-methylxanthene-9-carboxylate

HRID 630425

反応式

HRID 630425 の反応式
[CH:1]1[C:14]2[CH:13]([C:15]([O:17][CH3:18])=[O:16])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[Li+].[CH3:20]C([N-]C(C)C)C.IC.[Cl-].[NH4+]>C1COCC1>[CH3:20][C:13]1([C:15]([O:17][CH3:18])=[O:16])[C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[O:6][C:7]2[C:12]1=[CH:11][CH:10]=[CH:9][CH:8]=2

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 699662methyl 9H-xanthene-9-carboxylateHCID 2724682Lithium diisopropylamide

生成物 1

HCID 12068831Methyl 9-methylxanthene-9-carboxylate収率 75%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

3.25 g (13.53 mmol) of methyl 9H-xanthene-9-carboxylate are dissolved in 70 ml THF, the solution is cooled with an ice bath and 10.15 ml (20.29 mmol) of a 2M solution of LDA are added drop wise whilst keeping the temperature at 0° C. After stirring at room temperature for 1 hr, 1.68 ml (27.06 mmol) of iodomethane are added drop wise and the system is stirred at rt overnight. The solution is poured over excess of saturated solution of ammonium chloride and is extracted thrice with ethyl ether. After washing with brine, the solution is dried and concentrated to give a reddish residue which is purified by column chromatography (Cl3CH/hexane from 1:3 to 1:1) to give 2.6 g of the title compound (75% yield) as a white solid.

後処理

  1. temperaturethe solution is cooled with an ice bath
  2. customat 0° C
  3. stirringthe system is stirred at rt overnight
  4. extractionis extracted thrice with ethyl ether
  5. washAfter washing with brine
  6. customthe solution is dried
  7. concentrationconcentrated
  8. customto give a reddish residue which
  9. customis purified by column chromatography (Cl3CH/hexane from 1:3 to 1:1)

出典と根拠

ORDレコード
ord-489cca544c92488bb9474e4352f0fa2f
出典データセット
uspto-grants-2016_04
特許番号
US09315463B2

関連ノート

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