Dimethyl Disulfide → 4-Methoxy-2-(methylthio)benzo[d]oxazole

HRID 2186444

反応式

HRID 2186444 の反応式
C([Li])CCC.[CH3:6][O:7][C:8]1[C:13]2[N:14]=[CH:15][O:16][C:12]=2[CH:11]=[CH:10][CH:9]=1.[CH3:17][S:18]SC>O1CCCC1>[CH3:6][O:7][C:8]1[C:13]2[N:14]=[C:15]([S:18][CH3:17])[O:16][C:12]=2[CH:11]=[CH:10][CH:9]=1

参加物

5

反応物 3

HCID 12232Dimethyl DisulfideHCID 225009354-Methoxybenzo(d)oxazoleHCID 178418339Butyllithium

生成物 1

HCID 224566644-Methoxy-2-(methylthio)benzo[d]oxazole

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

n-Butyllithium (20.13 ml of a 1.6N solution in hexanes) was added gradually to a solution of 4-methoxybenzoxazole (4.0 g) in tetrahydrofuran (150 ml) cooled in a cardice-acetone bath under an atmosphere of nitrogen. After stirring for 20 minutes dimethyl disulfide (2.9 ml) was added. The mixture was warmed to room temperaturee and stirred for 18 hours. The tetrahydrofuran was removed by evaporation in vacuo and the residue partitioned between ethyl acetate (150 ml) and water (150 ml). The organics were washed with water (150 ml), dried over magnesium sulphate, filtered and the solvent removed in vacuo. Purification by column chromatography on silica eluting with 10% ethyl acetate in heptane afforded the title compound as a white solid (2.63 g).

後処理

  1. temperaturecooled in a cardice-acetone bath under an atmosphere of nitrogen
  2. additionwas added
  3. temperatureThe mixture was warmed to room temperaturee
  4. customThe tetrahydrofuran was removed by evaporation in vacuo
  5. customthe residue partitioned between ethyl acetate (150 ml) and water (150 ml)
  6. washThe organics were washed with water (150 ml)
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. customthe solvent removed in vacuo
  10. customPurification by column chromatography on silica eluting with 10% ethyl acetate in heptane

出典と根拠

ORDレコード
ord-a1f59b8e986e4c919f23d7f5721ce585
出典データセット
uspto-grants-2002_06
特許番号
US06403791B1

関連ノート

読み込み中…