HCID 13371411, compound → HCID 13371413, compound

HRID 1589140Notes

Reaction equation

HRID 1589140 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.[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 1118Sulfuric AcidSolvent

Procedure

To a solution of 4-fluoroestra-1,3,5(10)-trien-17β-ol (100 mg, 0.36 mmol) in 1.5 ml of acetone at 0° C. was added, dropwise with stirring, a solution of 95 ml of 8N chromium trioxide in 8N sulfuric acid. After approximately 5 min. the reaction mixture was poured into 75 ml of ice water and the solids were collected. The filter cake was stirred with methanol. The inorganic salts were removed and the filtrate was evaporated to dryness to give the crude product, 4-fluoroestra-1,3,5-(10)-trien-17-one as a tan solid. The latter was crystallized 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 δ 7.21-6.81 (m, 3, H1, H2, H3 aromatic) 2.91-1.54 (m, 15), 0.92 (s, 3, C18CH3).

Workup

  1. customthe solids were collected
  2. stirringThe filter cake was stirred with methanol
  3. customThe inorganic salts were removed
  4. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-5e65a0fd213b492d9ee56f56cdfd4375
Source dataset
uspto-grants-1986_02
Patent number
US04568673

Reaction notes

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