Hydrochloric Acid → HCID 22846444, compound

HRID 2254628Notes

Reaction equation

HRID 2254628 reaction equation
C(O[C@@H:5]1[C@H:10]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:8]2([CH3:9])[C:7](=[O:27])[CH2:6]1)[C@:19]1([CH3:20])[C:14]([C:15]([CH3:26])=[C:16]([O:24]C)[CH2:17][CH2:18]1)=[CH:13][CH2:12]3)(=O)C.[CH:28]#[CH:29].Cl>CO.O>[C:28]([C@:7]1([OH:27])[CH:6]=[CH:5][C@H:10]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:8]12[CH3:9])[C@:19]1([CH3:20])[C:14](=[C:15]([CH3:26])[C:16](=[O:24])[CH2:17][CH2:18]1)[CH2:13][CH2:12]3)#[CH:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6326AcetyleneHCID 53785297HCID 53785297, compound

Product 1

HCID 22846444HCID 22846444, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

3.5 g of 15α-acetoxy-3-methoxy-4-methylandrosta-3,5-dien-17-one is reacted with acetylene analogously to Example 5. The resultant 17α-ethynyl-3-methoxy-4-methylandrosta-3,5,15-trien-17β-ol is allowed to react, as described in Example 5with concentrated hydrochloric acid in a mixture of methanol/water. After the crude product has been chromatographed on silica gel with a hexane-ethyl acetate gradient, 1.3 g of 17α-ethynyl-17β-hydroxy-4methylandrosta-4,15-diene-3-one is obtained as a foam.

Workup

  1. customto react
  2. customAfter the crude product has been chromatographed on silica gel with a hexane-ethyl acetate gradient

Sources & evidence

ORD record
ord-3ae692a03ec244e38937df0bef85063d
Source dataset
uspto-grants-1993_08
Patent number
US05236912

Reaction notes

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