Water → 3-Hydroxy-2-methoxy-estra-1,3,5(10)-triene-17-thione

HRID 28343

反応式

HRID 28343 の反応式
[OH:1][C:2]1[C:19]([O:20][CH3:21])=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](=O)[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:32])=CC=1.O>C1(C)C=CC=CC=1>[OH:1][C:2]1[C:19]([O:20][CH3:21])=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](=[S:32])[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1

参加物

5

反応物 3

HCID 962WaterHCID 87949Lawesson's reagentHCID 4406242-Methoxyestrone

生成物 1

HCID 115948543-Hydroxy-2-methoxy-estra-1,3,5(10)-triene-17-thione収率 36%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of 1.09 g (3.63 mmol) of 3-hydroxy-2-methoxy-estra-1,3,5(10)-trien-17-one in 60 ml of toluene (abs.) was mixed with 3.7 g of Lawesson's reagent, and it was refluxed for four hours. After water was added, it was extracted with dichloromethane (3×), and the combined organic phases were washed with water, dried on sodium sulfate, and concentrated by evaporation in a rotary evaporator. Flash chromatography (n-hexane/ethyl acetate) yielded 412 mg (36%) of the desired product as yellow crystals.

後処理

  1. temperaturewas refluxed for four hours
  2. extractionit was extracted with dichloromethane (3×)
  3. washthe combined organic phases were washed with water
  4. customdried on sodium sulfate
  5. concentrationconcentrated by evaporation in a rotary evaporator

出典と根拠

ORDレコード
ord-2b87ae866ad34a3a88f8e4d53d11a509
出典データセット
uspto-grants-2008_09
特許番号
US07419972B2

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