Benzene → Cholest-4-ene-3,6-dione

HRID 726529ノート

反応式

HRID 726529 の反応式
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16](=[CH:17][C:18](=[O:28])[CH2:19][CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].N1CCCC1.C1C=CC=CC=1.C1(C[OH:47])C=CC=CC=1>C(O)(=O)C>[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16](=[CH:17][C:18](=[O:28])[CH2:19][CH2:20]2)[C:15](=[O:47])[CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:1]

参加物

6

反応物 4

HCID 241BenzeneHCID 244Benzyl AlcoholHCID 31268PyrrolidineHCID 91477Cholest-4-en-3-one2 回

生成物 1

HCID 101934Cholest-4-ene-3,6-dione

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

4-Cholesten-3,6-dione was prepared using 4-cholesten-3-one (Aldrich Co.) as a starting material by reference to the method of Hevl and Herr (F. W. Hevl and M. E. Herr, J. Am. Chem. Soc., 75: 1918, 1953) and that of Malhotra et al. (S. K. Malhotra, J. J. Hostynek and A. F. Lundin, J. Am. Chem. Soc., 90: 6565, 1968). Stated specifically, pyrrolidine (2.85 g) was added to a benzene solution (50 ml) of 4-cholesten-3-one (3.84 g) and the mixture was refluxed under heating for 24 hours. After cooling, the solvent and the excess pyrrolidine were distilled off under vacuum. Upon recrystallization from methanol, a colorless crystal of dienamine (4.16 g) was obtained. Cupric acetate (100 mg) was added to a benzene-methanol (500:10) solution of the dienamine (4.16 g) and air was introduced into the mixture for 24 hours. Then, a 2% aqueous solution (20 ml) of acetic acid was added and the mixture was stirred for 30 minutes and washed successively with water, a 1% sodium carbonate solution and a saturated saline solution. The resulting residue was dried, filtered and subjected to silica gel column chromatography (hexane:ethyl acetate=10:1) to yield a colorless crystal of 4-cholestene-3,6-dione (3.23 g).

後処理

  1. custom4-Cholesten-3,6-dione was prepared
  2. temperaturethe mixture was refluxed
  3. temperatureunder heating for 24 hours
  4. temperatureAfter cooling
  5. distillationthe solvent and the excess pyrrolidine were distilled off under vacuum
  6. customUpon recrystallization from methanol
  7. customa colorless crystal of dienamine (4.16 g) was obtained
  8. additionwas introduced into the mixture for 24 hours
  9. washwashed successively with water
  10. customThe resulting residue was dried
  11. filtrationfiltered

出典と根拠

ORDレコード
ord-e4f98466db954b0b83f432d6d8b6d72c
出典データセット
uspto-grants-1998_01
特許番号
US05710143

反応ノート

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