Hydrochloric Acid → 2-Methoxyestra-1,3,5(10)-triene-3-ol

HRID 1692558

反応式

HRID 1692558 の反応式
[CH3:1][C@@:2]12[C:18](=O)[CH2:17][CH2:16][C@H:15]1[C@H:14]1[C@@H:5]([C:6]3[C:11]([CH2:12][CH2:13]1)=[CH:10][C:9]([OH:20])=[C:8]([O:21][CH3:22])[CH:7]=3)[CH2:4][CH2:3]2.O.NN.[OH-].[K+].Cl>C(O)CO.C(O)CCC>[CH3:22][O:21][C:8]1[C:9]([OH:20])=[CH:10][C:11]2[CH2:12][CH2:13][C@@H:14]3[C@@H:5]([C:6]=2[CH:7]=1)[CH2:4][CH2:3][C@@:2]1([CH3:1])[C@H:15]3[CH2:16][CH2:17][CH2:18]1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 4406242-Methoxyestrone2 回

生成物 1

HCID 462273782-Methoxyestra-1,3,5(10)-triene-3-ol収率 72%

試薬・触媒・溶媒 2

HCID 174Ethylene Glycol溶媒HCID 2631-Butanol溶媒

反応条件

温度
130 °C

実験手順

2-Methoxyestrone (Scheme 1, Compound 4) (450 mg, 1.5 mmol) was suspended in ethylene glycol (10 mL) and n-butanol (2 mL). Hydrazine hydrate (0.145 mL, 3 mmol) was added and the mixture was heated to 130° C. for 1 h. The reaction was cooled to 70° C., KOH (253 mg, 4.5 mmol) was added, then the reaction vas heated at 200° C. for 1 h. The mixture was cooled to room temperature, poured into ice and HCl (6N, 6 mL) was added. The resulting solid was filtered off. The solid was dissolved in acetone, which was then evaporated to give a product (Scheme 1, Compound 7) (310 mg, 72% yield). 1H NMR (300 MHz, CDCl3) δ 6.93 (1H, s, aromatic), 6.75 (1H, s, aromatic), 5.35 (1H, s, phenol), 3.95 (3H, s, methoxy), 2.95 (2H, dd, J=5.0, 3.0 Hz), 2.25 (2H, m,), 1.95 (2H, m), 1.95-1.05 (11H, m), 0.8 (3H, s)

後処理

  1. temperatureThe reaction was cooled to 70° C.
  2. customthe reaction
  3. temperaturevas heated at 200° C. for 1 h
  4. temperatureThe mixture was cooled to room temperature
  5. additionwas added
  6. filtrationThe resulting solid was filtered off
  7. dissolutionThe solid was dissolved in acetone
  8. customwhich was then evaporated

出典と根拠

ORDレコード
ord-32f98cfc81f14cae87c69451d074bdc8
出典データセット
uspto-grants-2012_04
特許番号
US08158612B2

関連ノート

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