Oxalic acid dihydrate → Estra-5(10),16-dien-3-one

HRID 2270519Notes

Reaction equation

HRID 2270519 reaction equation
C[O:2][C:3]1[CH2:21][CH2:20][C@@:19]2(C)[C:5](=[CH:6][CH2:7][C@@H:8]3[C@@H:18]2[CH2:17][CH2:16][C@@:15]2([CH3:23])[C@H:9]3[CH2:10][CH2:11][C@@H:12]2C=C)[CH:4]=1.O.O.C(O)(=O)C(O)=O>CC(C)=O>[CH3:23][C@:15]12[CH2:16][CH2:17][C@H:18]3[C@@H:8]([CH2:7][CH2:6][C:5]4[CH2:4][C:3](=[O:2])[CH2:21][CH2:20][C:19]=43)[C@@H:9]1[CH2:10][CH:11]=[CH:12]2

Participants

4

Reactant 2

HCID 61373Oxalic acid dihydrateHCID 57012029Pregna-3,5,20-trien-3-yl methyl ether

Product 1

HCID 15870993Estra-5(10),16-dien-3-oneYield 75.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Estra-2,5(10), 16-triene-3-methyl ether (2) (646.3 mg, 2.390 mmole), dissolved in 50 ml of acetone was hydrolyzed for 6 h at room temperature using oxalic acid dihydrate (0.84 g, 6.7 mmole). The reaction mixture was quenched with 25 ml of saturated sodium bicarbonate and then extracted twice with 25 ml portions of ethyl acetate. The combined organic extracts were washed twice with 25 ml of brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was recrystallized from hexane to give product (462.5 mg, 1.804 mmole, 75%), m.p. 112-116 C.

Workup

  1. customThe reaction mixture was quenched with 25 ml of saturated sodium bicarbonate
  2. extractionextracted twice with 25 ml portions of ethyl acetate
  3. washThe combined organic extracts were washed twice with 25 ml of brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-b64f04ff2d704e469beed90f2db842ae
Source dataset
uspto-grants-2001_12
Patent number
US06331534B1

Reaction notes

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