Pyridine → Estra-1,3,5,7,9,16-hexaen-3-YL acetate
Reaction equation
[CH3:1][C@:2]12[CH2:18][CH2:17][C:16]3[C:15]4[CH:14]=[CH:13][C:12]([OH:19])=[CH:11][C:10]=4[CH:9]=[CH:8][C:7]=3[C@@H:6]1[CH2:5][CH:4]=[CH:3]2.N1C=CC=CC=1.[C:26](OC(=O)C)(=[O:28])[CH3:27]>C(OCC)(=O)C>[C:26]([O:19][C:12]1[CH:13]=[CH:14][C:15]2[C:16]3[CH2:17][CH2:18][C@@:2]4([CH3:1])[C@@H:6]([CH2:5][CH:4]=[CH:3]4)[C:7]=3[CH:8]=[CH:9][C:10]=2[CH:11]=1)(=[O:28])[CH3:27]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of estra-1,3,5(10),6,8,16-hexaen-3-ol Q8, 148.8 mg, 0.5944 mmol) in anh. pyridine (2.0 mL, 25 mmol) and acetic anhydride (0.28 mL, 3.0 mmol) was stirred 6 h, after which ethyl acetate (20 mL) was added. See FIG. 16. The mixture was washed with three 10 mL portions of 1N hydrochloric acid+10 mL of saturated sodium bicarbonate+10 mL of brine, dried over sodium sulfate, and filtered. The residue was washed with 5 mL of ethyl acetate and the combined filtrates were concentrated under reduced pressure. Recrystallization from 95% ethanol gave lustrous white platelets (99.4 mg, 0.340 mmol, 55%, m.p. 95°-96° C. TLC (2% ethyl acetate/hazanes on silica gel) showed product (Rf 0.1) contained a trace contaminant at the origin.
Workup
- washThe mixture was washed with three 10 mL portions of 1N hydrochloric acid+10 mL of saturated sodium bicarbonate+10 mL of brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- washThe residue was washed with 5 mL of ethyl acetate
- concentrationthe combined filtrates were concentrated under reduced pressure
- customRecrystallization from 95% ethanol
- customgave lustrous white platelets (99.4 mg, 0.340 mmol, 55%, m.p. 95°-96° C
Sources & evidence
- ORD record
- ord-468cb3245f1d495c916c0c2155cad422
- Source dataset
- uspto-grants-1997_05
- Patent number
- US05633392
Reaction notes
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