Reaction #56621

ord-2b87ae866ad34a3a88f8e4d53d11a509

Reaction equation

O
water
COc1cc2c(cc1O)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
3-hydroxy-2-methoxy-estra-1,3,5(10)-trien-17-one
COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1
Lawesson's reagent
→
COc1cc2c(cc1O)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=S)CC[C@@H]12
desired product
Yield 36.0%
COc1cc2c(cc1O)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=S)CC[C@@H]12
3-Hydroxy-2-methoxy-estra-1,3,5(10)-triene-17-thione
Yield 36.0%

Reactants

O
water
COc1cc2c(cc1O)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
3-hydroxy-2-methoxy-estra-1,3,5(10)-trien-17-one
COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1
Lawesson's reagent

Reagents

None

Solvents

Cc1ccccc1
toluene

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturewas refluxed for four hours
  2. 2
    Extractionit was extracted with dichloromethane (3×)
  3. 3
    Washthe combined organic phases were washed with water
  4. 4
    Otherdried on sodium sulfate
  5. 5
    Concentrationconcentrated by evaporation in a rotary evaporator

Procedure

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07419972B2uspto-grants-2008_09