Hydrochloric Acid → 4-Methyl-4-androsten-3,17-dione

HRID 1200173

反応式

HRID 1200173 の反応式
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH2:9][C:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C:12](=[O:20])[CH:11]=4)[C@@H:6]1[CH2:5][CH2:4][C:3]2=[O:21].[CH3:22]C(C)([O-])C.[K+].CCl.Cl>C(O)(C)(C)C.O>[CH3:22][C:11]1[C:12](=[O:20])[CH2:13][CH2:14][C@@:15]2([CH3:16])[C:10]=1[CH2:9][CH2:8][C@@H:7]1[C@@H:17]2[CH2:18][CH2:19][C@@:2]2([CH3:1])[C@H:6]1[CH2:5][CH2:4][C:3]2=[O:21]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 6128AndrostenedioneHCID 6327Methyl ChlorideHCID 23665647Potassium tert-butoxide

生成物 1

HCID 147309424-Methyl-4-androsten-3,17-dione

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6386tert-Butanol溶媒3 回

実験手順

A solution of androst-4-ene-3,17-dione in t-butanol was heated to boiling and added to a boiling solution of potassium t-butoxide in t-butanol. Methyl chloride in t-butanol was added slowly. The solution was cooled, acidified with concentrated hydrochloric acid, and diluted with water. The excess t-butanol was removed under vacuum and the aqueous layer extracted with ethylacetate. The combined extracts were washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel and eluted with hexane/ethylacetate. The eluant was evaporated and the residue crystallized from ether to yield 4-methylandrost-4-ene-3,17-dione; I.R. (KBr): 1735 (17-oxo), 1660 (3-oxo), 1620 cm-1 (Δ4).

後処理

  1. temperatureThe solution was cooled
  2. customThe excess t-butanol was removed under vacuum
  3. extractionthe aqueous layer extracted with ethylacetate
  4. washThe combined extracts were washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica gel
  8. washeluted with hexane/ethylacetate
  9. customThe eluant was evaporated
  10. customthe residue crystallized from ether

出典と根拠

ORDレコード
ord-ac90653361494d16bb9441bd53d48655
出典データセット
uspto-grants-1990_02
特許番号
US04904650

関連ノート

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