Ethyl orthoformate → 3-Ethoxy-androsta-3,5-dien-17-one
Reaction equation
O[C@@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH:14]=[CH:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C@:4]1([CH3:22])[CH:9]([CH2:10][CH2:11]2)[CH2:8][C:7](=[O:21])[CH2:6][CH2:5]1.O.[C:24]1(C)C(S(O)(=O)=O)=CC=C[CH:29]=1.C(OCC)(OCC)OCC>C(O)C>[CH2:24]([O:21][C:7]1[CH2:6][CH2:5][C@@:4]2([CH3:22])[C:9](=[CH:10][CH2:11][C@@H:12]3[C@@H:3]2[CH2:2][CH2:19][C@@:17]2([CH3:18])[C@H:13]3[CH2:14][CH2:15][C:16]2=[O:20])[CH:8]=1)[CH3:29]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
11α-Hydroxyandrostendione (429.5 g) and toluene sulfonic acid hydrate (7.1) were charged to a reaction flask under nitrogen. Ethanol (2.58 L) was added to the reactor, and the resulting solution cooled to 5° C. Triethyl orthoformate (334.5 g) was added to the solution over a 15 minute period at 0° to 15° C. After the triethyl orthoformate addition was complete the reaction mixture was warmed to 40° C. and reacted at that temperature for 2 hours, after which the temperature was increased to reflux and reaction continued under reflux for an additional 3 hours. The reaction mixture was cooled under vacuum and the solvent removed under vacuum to yield 3-ethoxyandrosta-3,5-diene-17-one.
Workup
- temperaturewas warmed to 40° C.
- customreacted at that temperature for 2 hours
- temperatureafter which the temperature was increased
- temperatureto reflux
- customreaction
- temperatureunder reflux for an additional 3 hours
- temperatureThe reaction mixture was cooled under vacuum
- customthe solvent removed under vacuum
Sources & evidence
- ORD record
- ord-e4182a82e2bb47dca24b5e8bd9f0d4c7
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06258946B1
Reaction notes
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