Sulfuric Acid → HCID 22791426, compound

HRID 918032Notes

Reaction equation

HRID 918032 reaction equation
[F:1][C@:2]12[C@@H:19]([OH:20])[CH2:18][C@@:16]3([CH3:17])[C@@H:12]([CH2:13][CH2:14][C:15]3=[O:21])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:23])[CH2:4][CH2:5][C:6](=[O:22])[CH:7]=1.[CH2:24](OC(OCC)OCC)[CH3:25].S(=O)(=O)(O)O>O1CCOCC1>[CH2:24]([O:22][C:6]1[CH2:5][CH2:4][C@@:3]2([CH3:23])[C:8](=[CH:9][CH2:10][C@@H:11]3[C@:2]2([F:1])[C@@H:19]([OH:20])[CH2:18][C@@:16]2([CH3:17])[C@H:12]3[CH2:13][CH2:14][C:15]2=[O:21])[CH:7]=1)[CH3:25]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 31214Ethyl orthoformateHCID 23616821357-09-5

Product 1

HCID 22791426HCID 22791426, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To 1 gm. of 9α-fluoro-11β-hydroxy-4-androstene-3,17 -dione in a solution of 1 ml. of triethylorthoformate in 7 ml. of dioxane add 0.6 ml. of 5% concentrated sulfuric acid in dioxane. Stir at room temperature for five minutes then add 1 ml. of pyridine and evaporate in vacuo to a residue. Add cold ethanol and filter off the resultant precipitate comprising 3-ethoxy-9α-fluoro-11β-hydroxy-3,5 -androstadiene- 3,17-dione (0.8 gm.).

Workup

  1. additionthen add 1 ml
  2. customof pyridine and evaporate in vacuo to a residue
  3. additionAdd cold ethanol
  4. filtrationfilter off the resultant precipitate

Sources & evidence

ORD record
ord-8873036785b94281a303914bd8376455
Source dataset
uspto-grants-1976_07
Patent number
US03968132

Reaction notes

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