Butanethiol → 6-(6-Hydroxy-2-naphthyl)-6-oxohexanoic acid

HRID 2118984

反応式

HRID 2118984 の反応式
C(SCCCC)CCC.[H-].[Na+].C(S)CCC.C[O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[CH:25]=[C:24]([C:29](=[O:37])[CH2:30][CH2:31][CH2:32][CH2:33][C:34]([OH:36])=[O:35])[CH:23]=[CH:22]2.C(SC)CCC>CN(C=O)C.O>[OH:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[CH:25]=[C:24]([C:29](=[O:37])[CH2:30][CH2:31][CH2:32][CH2:33][C:34]([OH:36])=[O:35])[CH:23]=[CH:22]2

参加物

8

反応物 5

HCID 8012ButanethiolHCID 11002Dibutyl sulfideHCID 12339Butyl methyl sulfideHCID 24758Sodium hydrideHCID 144259056-(6-Methoxy-2-naphthyl)-6-oxo-hexanoic acid

生成物 1

HCID 139825416-(6-Hydroxy-2-naphthyl)-6-oxohexanoic acid収率 79%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒3 回

実験手順

Butyl sulfide was generated by placing NaH (2.57 g, 0.11 mol) in a 500 ml round bottom flask, adding butanethiol (5.14 ml, 0.48 mol) and stirring for 5 minutes. DMF (200 mls) was added and the reaction heated at reflux. Slowly, 6-(6-methoxy-2-naphthyl)-6-oxo-hexanoic acid (Example 5) (7.2 g, 0.25 mol) in DMF (100 ml) was added to the reaction and heated at reflux for 1 hour. The methyl butyl sulfide and DMF were vacuum distilled (7 torr, 28° C.) to leave a bright yellow powder that was dissolved in water and precipitated with 5% HCl. The precipitate was filtered, dissolved in ethyl acetate (1800 ml), dried (Na2SO4), filtered and evaporated to give a yellow solid that was recrystallized (ethyl acetate) to give the title compound (5.38 grams, 79% yield), mp 191-193° C.; MS, m/e 272 (M+).

後処理

  1. temperaturethe reaction heated
  2. temperatureat reflux
  3. temperatureheated
  4. temperatureat reflux for 1 hour
  5. distillationdistilled (7 torr, 28° C.)
  6. customto leave a bright yellow powder that
  7. customprecipitated with 5% HCl
  8. filtrationThe precipitate was filtered
  9. dissolutiondissolved in ethyl acetate (1800 ml)
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. customevaporated
  13. customto give a yellow solid
  14. customthat was recrystallized (ethyl acetate)

出典と根拠

ORDレコード
ord-44b9dc72756947e5b297b36a944c8769
出典データセット
uspto-grants-1987_07
特許番号
US04681894

関連ノート

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