Acetic Anhydride → HCID 86738324, compound

HRID 2059303Notes

Reaction equation

HRID 2059303 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:17]([CH2:18][CH2:19][C@:3]12[CH3:4])[C@:16]1([CH2:20][C:21]#[CH:22])[C:11](=[CH:12][C:13](=[O:23])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3.[C:24](OC(=O)C)(=[O:26])[CH3:25]>N1C=CC=CC=1>[C:24]([O:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:17]([CH2:18][CH2:19][C@:3]12[CH3:4])[C@:16]1([CH2:20][C:21]#[CH:22])[C:11](=[CH:12][C:13](=[O:23])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3)(=[O:26])[CH3:25]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 86738323HCID 86738323, compound

Product 1

HCID 86738324HCID 86738324, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 500 mg of 17β-hydroxy-10-(2-propynyl)estr-4-en-3-one in 4 ml of pyridine at 25° C. is added 4 ml of acetic anhydride and the mixture is allowed to stand at room temperature for 16 hours. It is then concentrated under reduced pressure, the residue is diluted with ether and the ether solution is washed with 1 N hydrochloric acid and with aqueous sodium bicarbonate and then dried and concentrated. The resultant residue is recrystallized from ethyl acetate-hexane to give 17β-acetoxy-10-(2-propynyl)estr-4-en-3-one. This compound has the following structural formula ##STR10##

Workup

  1. concentrationIt is then concentrated under reduced pressure
  2. additionthe residue is diluted with ether
  3. washthe ether solution is washed with 1 N hydrochloric acid and with aqueous sodium bicarbonate
  4. customdried
  5. concentrationconcentrated
  6. customThe resultant residue is recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-d464cc13a68645ad85b336cfb766da39
Source dataset
uspto-grants-1982_03
Patent number
US04322416

Reaction notes

Loading…