Methyl iodide → HCID 86733696, compound

HRID 918057Notes

Reaction equation

HRID 918057 reaction equation
[C:1]([O:4][C@@H:5]1[CH2:25][CH2:24][C@@:23]2([CH3:26])[C@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:22]2[C:21](=[O:27])[CH2:20][C@@:19]2([CH3:28])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C:15](=[O:18])[CH2:16][OH:17])[CH2:6]1)(=[O:3])[CH3:2].[CH3:29]I>[Ag]=O>[C:1]([O:4][C@@H:5]1[CH2:25][CH2:24][C@@:23]2([CH3:26])[C@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:22]2[C:21](=[O:27])[CH2:20][C@@:19]2([CH3:28])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C:15](=[O:18])[CH2:16][O:17][CH3:29])[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 86733697HCID 86733697, compound

Product 1

HCID 86733696HCID 86733696, compound

Reagents, catalysts & solvents 1

HCID 92152Silver(II) oxideCatalyst

Procedure

Freshly prepared silver oxide (690 mg.) was added to a solution of 3α-acetoxy-21-hydroxy-5β-pregnane-11,20-dione (68.3 mg.) in methyl iodide (1.5 ml.) and the resulting mixture was refluxed for 1 hour, allowed to stand overnight and then refluxed for a further 3 hours. The reaction was partitioned between water and chloroform and the chloroform layer was washed with water, dried (Na2SO4) and evaporated to give 3α-acetoxy-21-methoxy-5β-pregnane-11,20-dione (69 mg.) as a foam. This was dissolved in methanol (1.25 ml.) and refluxed with 10% aqueous potassium bicarbonate solution (0.6 ml.) for 2.5 hours. The reaction mixture was allowed to cool and was partitioned between water and ether. The ether layer was washed with water, dried (Na2SO4) and evaporated. The product was purified by preparative t.l.c. (ethyl acetate:chloroform; 1:1) to give the title compound as a foam, [α]D + 80°, (c 2.36).

Workup

  1. temperaturethe resulting mixture was refluxed for 1 hour
  2. temperaturerefluxed for a further 3 hours
  3. customThe reaction was partitioned between water and chloroform
  4. washthe chloroform layer was washed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-25d0637601314bc0bc555b9d959b5a9e
Source dataset
uspto-grants-1976_07
Patent number
US03969345

Reaction notes

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