Acetic Anhydride → HCID 70046766, compound

HRID 652217Notes

Reaction equation

HRID 652217 reaction equation
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:16]2[C@@H:15]([OH:21])[CH2:14][C@@:12]2([CH3:13])[C@H:8]3[C@@H:9]3[CH2:23][C@@H:10]3[C:11]2=[O:22])[CH2:3]1.[C:24](OC(=O)C)(=[O:26])[CH3:25]>N1C=CC=CC=1>[C:24]([O:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:16]2[C@@H:15]([OH:21])[CH2:14][C@@:12]2([CH3:13])[C@H:8]3[C@@H:9]3[CH2:23][C@@H:10]3[C:11]2=[O:22])[CH2:3]1)(=[O:26])[CH3:25]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 70445995HCID 70445995, compound

Product 1

HCID 70046766HCID 70046766, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 7.9 g of 3β,11β-dihydroxy-15β,16β-methyleneandrost-5-en-17-one in 39.5 ml of pyridine and 39.5 ml of acetic anhydride is left to stand at room temperature for 5 hours, diluted with 800 ml of ice-water and, after standing for 1 hour, extracted with ethyl acetate. The organic phase is washed in succession with saturated sodium chloride solution, ice-cold dilute hydrochloric acid, ice-cold dilute sodium hydroxide solution and again with saturated sodium chloride solution, dried, and concentrated under a water-jet vacuum. Chromatography of the crude product over 30 times the amount by weight of silica gel and elution with a mixture of methylene chloride/acetone (98:2) yield 3β-acetoxy-11β-hydroxy-15β,16β-methyleneandrost-5-en-17-one which, after being dissolved and recrystallised once from methylene chloride/ether/petroleum ether, melts at 209°-211°.

Workup

  1. waitafter standing for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed in succession with saturated sodium chloride solution, ice-cold dilute hydrochloric acid, ice-cold dilute sodium hydroxide solution and again with saturated sodium chloride solution
  4. customdried
  5. concentrationconcentrated under a water-jet vacuum
  6. washChromatography of the crude product over 30 times the amount by weight of silica gel and elution
  7. additionwith a mixture of methylene chloride/acetone (98:2)

Sources & evidence

ORD record
ord-964c4e942f174d2bac675cd737af6148
Source dataset
uspto-grants-1987_06
Patent number
US04670551

Reaction notes

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