Acetic Acid → HCID 68729360, compound

HRID 1182888Notes

Reaction equation

HRID 1182888 reaction equation
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH:9]=[C:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C:12](=[O:20])[CH2:11]4)[C@@H:6]1[CH2:5][CH2:4][C:3]2=[O:21].[CH3:22][C:23]([OH:25])=[O:24]>C1(C)C=CC=CC=1>[C:23]([O:25][C@@H:11]1[C:12](=[O:20])[CH2:13][CH2:14][C@@:15]2([CH3:16])[C:10]1=[CH:9][CH2:8][C@@H:7]1[C@@H:17]2[CH2:18][CH2:19][C@@:2]2([CH3:1])[C@H:6]1[CH2:5][CH2:4][C:3]2=[O:21])(=[O:24])[CH3:22]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 160531Androst-5-ene-3,17-dione

Product 1

HCID 68729360HCID 68729360, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of androst-5-ene-3,17-dione (2.00 g) in toluene (10 ml) at 15° C., AcOH (10 ml) and LTA (3.40 g) were added. After stirring for 2 h, the mixture was warmed to RT and stirred for 24 h. The reaction was quenched by addition of H2O and extracted three times with EtOAc. The combined organic extracts were washed with H2O, brine, dried over Na2SO4, and evaporated to dryness. The crude product was purified by triturating with a 1:1 mixture of n-hexane:EtOAc (3 ml) to give 4α-acetoxyandrost-5-ene-3,17-dione (600 mg, 25%).

Workup

  1. stirringstirred for 24 h
  2. customThe reaction was quenched by addition of H2O
  3. extractionextracted three times with EtOAc
  4. washThe combined organic extracts were washed with H2O, brine
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness
  7. customThe crude product was purified
  8. customby triturating with a 1:1 mixture of n-hexane

Sources & evidence

ORD record
ord-a2ef1727089a4a76ade5b246c44b5da4
Source dataset
uspto-grants-2014_03
Patent number
US08664210B2

Reaction notes

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