Water → HCID 13578828, compound

HRID 1285312Notes

Reaction equation

HRID 1285312 reaction equation
[OH2:1].C[C:3]1[C:20]2[C@:15]([CH3:22])([CH2:16][CH2:17][C:18](=[O:21])[CH:19]=2)[C@@H:14]2[C@H:5]([C@H:6]3[C@@:10]([CH2:12][CH2:13]2)([CH3:11])[C:9](=[O:23])[C:8](=[CH2:24])[CH2:7]3)[CH:4]=1.[CH2:25]1COC[CH2:26]1>S(=O)(=O)(O)O.CO>[C:25]([C@:9]1([OH:23])[C:8](=[CH2:24])[CH2:7][C@H:6]2[C@H:5]3[C:14](=[CH:13][CH2:12][C@:10]12[CH3:11])[C@:15]1([CH3:22])[C:20](=[CH:19][C:18](=[O:21])[CH2:17][CH2:16]1)[CH2:3][CH2:4]3)(=[O:1])[CH3:26]

Participants

6

Reactant 3

HCID 962WaterHCID 8028TetrahydrofuranHCID 54425312HCID 54425312, compound

Product 1

HCID 13578828HCID 13578828, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1118Sulfuric AcidSolvent

Procedure

The mercuric oxide (red, 1.2 g), which had been dissolved in concentrated sulfuric acid (1.6 ml) and water (25 ml) was added to a solution of 17α-ethinyl-17β-hydroxy-16-methyleneandrosta-4,9(11)-dien-3-one (IVA, Example 11, 10 g) in methanol (600 ml) and THF (125 ml). The reaction mixture was stirred overnight at 20°-25° at which time the reaction was complete as measured by TLC. The solids were removed by filtration through a Celite pad. The filtrate was concentrated under reduced pressure to a solid which was triturated with methanol (25 ml). The mixture was filtered and the solids dried to give the title compound, m.p. 147°-162°; NMR (CDCl3) 0.88, 1.35, 2.35, 5.02, 5.50 and 5.75 δ.

Workup

  1. customThe solids were removed by filtration through a Celite pad
  2. concentrationThe filtrate was concentrated under reduced pressure to a solid which
  3. customwas triturated with methanol (25 ml)
  4. filtrationThe mixture was filtered
  5. customthe solids dried

Sources & evidence

ORD record
ord-9ab58cd25f96473b9da84d1a3f322c81
Source dataset
uspto-grants-1986_01
Patent number
US04567001

Reaction notes

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