Hydrochloric Acid → Estra-1,3,5(10),6-tetraen-3-ol

HRID 1604744ノート

反応式

HRID 1604744 の反応式
[CH3:1][C@:2]12[CH2:18][CH2:17][C@H:16]3[C@@H:7]([CH:8]=[CH:9][C:10]4[CH:11]=[C:12]([OH:19])[CH:13]=[CH:14][C:15]=43)[C@@H:6]1[CH2:5][CH2:4][C:3]2=O.NN.[OH-].[K+].Cl>C(O)COCCO.O>[CH3:1][C@:2]12[CH2:18][CH2:17][C@H:16]3[C@@H:7]([CH:8]=[CH:9][C:10]4[CH:11]=[C:12]([OH:19])[CH:13]=[CH:14][C:15]=43)[C@@H:6]1[CH2:5][CH2:4][CH2:3]2

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 14797Potassium HydroxideHCID 1022253-Hydroxyestra-1,3,5(10),6-tetraen-17-one

生成物 1

HCID 15480542Estra-1,3,5(10),6-tetraen-3-ol

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8117Diethylene Glycol溶媒

実験手順

Estra-1,3,5(10),6-tetraen-3-ol-17-one (91.1 mg, 0.339 mmol), hydrazine (54 μL, 1.7 mmol), and potassium hydroxide (0.06 g) in 1.8 mL of diethylene glycol were heated in a 200° C. bath under argon for 2 h. After cooling to RT 10 mL of water were added and the solution was acidified to pH≈2 with 1N HCl. The resulting suspension was extracted three times with 10 mL of ether and the combined organic extracts were washed with 10 mL of brine, dried over magnesium sulfate, filtered through Celite, and concentrated under reduced pressure. The crude solid was purified by preparative TLC (25% ethyl acetate/hexane on silica gel) to give product homogeneous to TLC (5.9 mg, 23 μmol, 7%).

後処理

  1. additionwere added
  2. extractionThe resulting suspension was extracted three times with 10 mL of ether
  3. washthe combined organic extracts were washed with 10 mL of brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered through Celite
  6. concentrationconcentrated under reduced pressure
  7. customThe crude solid was purified by preparative TLC (25% ethyl acetate/hexane on silica gel)
  8. customto give product homogeneous to TLC (5.9 mg, 23 μmol, 7%)

出典と根拠

ORDレコード
ord-b744f3e3d60a4b7e8d3ce4ad8fd639be
出典データセット
uspto-grants-1999_11
特許番号
US05994568

反応ノート

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