Hydrochloric Acid → Estra-1,3,5(10),7-tetraene-3,17alpha-diol diacetate
Reaction equation
[CH3:1][C@@:2]12[C@H:19]([OH:20])[CH2:18][CH2:17][C@H:16]1[C:6]1=[CH:7][CH2:8][C:9]3[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:10]=3[C@H:5]1[CH2:4][CH2:3]2.[C:21]1([CH3:31])C=CC(S(O)(=O)=O)=CC=1.[C:32](OC(=O)C)(=[O:34])[CH3:33].Cl.[OH2:40]>N1C=CC=CC=1>[C:32]([O:15][C:13]1[CH:12]=[CH:11][C:10]2[C@@H:5]3[C:6]([C@H:16]4[C@@:2]([CH2:3][CH2:4]3)([CH3:1])[C@H:19]([O:20][C:21](=[O:40])[CH3:31])[CH2:18][CH2:17]4)=[CH:7][CH2:8][C:9]=2[CH:14]=1)(=[O:34])[CH3:33]Participants
7
Conditions
- Temperature
- 60 °C
Procedure
17α-Dihydroequilin (1 g), p-toluenesulfonic acid (1 g), and acetic anhydride (40 ml) were heated in an oil bath at 100° C. until a clear solution was obtained and then left at room temperature in the dark for 2 days. At this time TLC showed no detectable amount of 17α-dihydroequilin. The mixture was poured into a solution of pyridine (30 ml) and water (400 ml), acidified with 4 N hydrochloric acid and extracted with diethyl ether (300 ml). The ether phase was washed with water (150 ml) and evaporated to dryness in vacuo. The product was dissolved in methanol (75 ml), heated to 60° C. and water (40 ml) added. After cooling, 1.14 g of 1,3,5(10),7-estratetraene-3,17α-diol 3,17-diacetate was obtained, m.p. 124°-126° C.
Workup
- customwas obtained
- extractionextracted with diethyl ether (300 ml)
- washThe ether phase was washed with water (150 ml)
- customevaporated to dryness in vacuo
- dissolutionThe product was dissolved in methanol (75 ml)
- additionwater (40 ml) added
- temperatureAfter cooling
Sources & evidence
- ORD record
- ord-d9d09e4b9e48433e81cc4c1cdd58b353
- Source dataset
- uspto-grants-1983_04
- Patent number
- US04379780
Reaction notes
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