Dichloromethane → 3-Methoxy-17-trimethylsilyloxy-estra-1,3,5(10),16-tetraene

HRID 373043

Reaction equation

HRID 373043 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@H:9]4[C@@:13]([CH2:15][CH2:16]3)([CH3:14])[C:12](=[O:21])[CH2:11][CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1.C(Cl)Cl.[CH3:25][Si:26](OS(C(F)(F)F)(=O)=O)([CH3:28])[CH3:27]>C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@H:9]4[C@@:13]([CH2:15][CH2:16]3)([CH3:14])[C:12]([O:21][Si:26]([CH3:28])([CH3:27])[CH3:25])=[CH:11][CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 65367Trimethylsilyl triflateHCID 92895(+)-Estrone 3-methyl ether

Product 1

HCID 155961703-Methoxy-17-trimethylsilyloxy-estra-1,3,5(10),16-tetraene

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

10 g of 3-methoxy-estra-1,3,5(10)-trien-17-one (35.2 mmol) is mixed with exclusion of moisture under inert gas with 30 ml of methylene chloride distilled on P2O5 and 10.5 g of trifluoromethanesulfonic acid trimethylsilyl ester (47.2 mmol, D=1.15). Then, about 7 ml of triethylamine (KOH dried, M=101.2; D=0.726) is added in portions with stirring and gentle cooling, and the solution reacts clearly in an alkaline way. Then, it is allowed to stand for 12 hours at room temperature, and after the reaction has been completed, the solvent is removed in a vacuum. The remaining viscous residue is extracted three times with about 20 ml of absolute ether under inert gas. The ether solution, in which the steroid is present, is used directly in the next step.

Workup

  1. customgentle cooling, and the solution reacts clearly in an alkaline way
  2. customthe solvent is removed in a vacuum
  3. extractionThe remaining viscous residue is extracted three times with about 20 ml of absolute ether under inert gas

Sources & evidence

ORD record
ord-ca4e0fc190c44465b461f289ddf0d46d
Source dataset
uspto-grants-1992_11
Patent number
US05162312

Linked notes

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