HCID 13371411, compound → HCID 13371413, compound

HRID 2413116Notes

Reaction equation

HRID 2413116 reaction equation
[F:1][C:2]1[C:3]2[CH2:4][CH2:5][C@@H:6]3[C@@H:15]([C:16]=2[CH:17]=[CH:18][CH:19]=1)[CH2:14][CH2:13][C@@:11]1([CH3:12])[C@H:7]3[CH2:8][CH2:9][C@@H:10]1[OH:20]>CC(C)=O.S([O-])([O-])(=O)=O.[NH4+].[NH4+].[O-2].[O-2].[O-2].[Cr+6]>[F:1][C:2]1[C:3]2[CH2:4][CH2:5][C@@H:6]3[C@@H:15]([C:16]=2[CH:17]=[CH:18][CH:19]=1)[CH2:14][CH2:13][C@@:11]1([CH3:12])[C@H:7]3[CH2:8][CH2:9][C:10]1=[O:20]

Participants

5

Reactant 1

HCID 13371411HCID 13371411, compound

Product 1

HCID 13371413HCID 13371413, compound

Reagents, catalysts & solvents 3

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolventHCID 6097028Ammonium SulfateSolvent

Procedure

To a solution of 4-fluoroestra-1,3,5-(10)-trien-17β-ol IV as prepared in Example 2 (100 mg, 0.36 mmol) in 1.5 ml of acetone at 0° C. is added, dropwise with stirring, a solution of (95ml) of 8N chromium trioxide in ammonium sulfate. After approximately 5 min. the reaction mixture is poured into 75 ml of ice-water and the solids are collected. The filter cake is stirred with methanol, the inorganic salts are removed and the filtrate is evaporated to dryness to give the crude product, 4-fluoroestra-1,3,5-(10)-trien-17-one as a tan solid. The latter crystallizes from ether-petroleum ether (30°-60°) as a colorless solid (60 mg, 61% yield), mp 139°-141° C. Ir (KBr)cm-1 1724 (C17C=O), 1230 (aryl fluoride); 1H NMR δ7.21-6.81 (m, 3, H1, H2, H3 aromatic) 2.91-1.54 (m, 15), 0.92 (s, 3, C18CH3). Anal. Calc'd. for C, 79.38; H, 7.77; F, 6.98. Found: C, 79.53; H, 7.76; F, 7.13.

Workup

  1. additionis added
  2. customthe solids are collected
  3. stirringThe filter cake is stirred with methanol
  4. customthe inorganic salts are removed
  5. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-9dc5d99212e447df95fccf18188dd15c
Source dataset
uspto-grants-1985_01
Patent number
US04496555

Reaction notes

Loading…