Methane → 1-Acetoxy-3,17beta-dimethoxy-1,3,5(10)-estratriene

HRID 839747Notes

Reaction equation

HRID 839747 reaction equation
[C:1]([O:4][C:5]1[C:22]2[C@@H:21]3[C@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C@@H:16]([OH:23])[CH2:15][CH2:14]4)[CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]([O:24][CH3:25])[CH:6]=1)(=[O:3])[CH3:2].C.N([CH2:29]NC(N)=O)=O.[H+].[B-](F)(F)(F)F>C(Cl)Cl>[C:1]([O:4][C:5]1[C:22]2[C@@H:21]3[C@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C@@H:16]([O:23][CH3:29])[CH2:15][CH2:14]4)[CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]([O:24][CH3:25])[CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 297MethaneHCID 28118Tetrafluoroboric acidHCID 104823Urea, (nitrosomethyl)-HCID 706142631-Acetoxy-3-methoxyestra-1,3,5(10)-trien-17beta-ol

Product 1

HCID 228038601-Acetoxy-3,17beta-dimethoxy-1,3,5(10)-estratriene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Acetoxy-3-methoxyestra-1,3,5(10)-trien-17β-ol (1.0 g) is etherified with CH2H2, generated from N-nitrosomethylurea and catalyzed with a drop of 48% HBF4 in methylene chloride. The resulting polymethylene polymer is filtered and the methylene chloride filtrate is washed with 10% sodium bicarbonate solution, water and then dried over sodium sulfate. Evaporation in vacuo gives an oil which is crystallized from ethanol to give 1-acetoxy-3,17β-dimethoxy-1,3,5(10)-estratriene as a white solid, yield 0.78 g (75%); m.p. 81°-83° C.

Workup

  1. filtrationThe resulting polymethylene polymer is filtered
  2. washthe methylene chloride filtrate is washed with 10% sodium bicarbonate solution, water
  3. dry with materialdried over sodium sulfate
  4. customEvaporation in vacuo
  5. customgives an oil which
  6. customis crystallized from ethanol

Sources & evidence

ORD record
ord-02747e2b414d45018a7825c5fc03bffd
Source dataset
uspto-grants-1978_06
Patent number
US04096253

Reaction notes

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