Hydrogen Peroxide → HCID 86738327, compound
Reaction equation
[CH2:1]([C@@:4]12[C@@H:21]3[C@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C:16](=[O:22])[CH2:15][CH2:14]4)[CH2:11][CH2:10][C:9]1=[CH:8][C:7](=[O:23])[CH2:6][CH2:5]2)[C:2]#[CH:3].[OH:24]O.[OH-].[Na+]>CO.O.[Cl-].[Na+].O>[O:24]1[C@:9]23[C@:4]([CH2:1][C:2]#[CH:3])([CH2:5][CH2:6][C:7](=[O:23])[CH:8]12)[C@@H:21]1[C@H:12]([C@H:13]2[C@@:17]([CH2:19][CH2:20]1)([CH3:18])[C:16](=[O:22])[CH2:15][CH2:14]2)[CH2:11][CH2:10]3Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 650 mg of 10-(2-propynyl)estr-4-ene-3,17-dione in 5 ml of methanol at 15° C. is added 0.6 ml of 30% hydrogen peroxide. A solution of 46 mg of sodium hydroxide in 0.4 ml of water is then added dropwise. After 1 hour at 15° C., the solution is stirred for 2 hours at 25° C. before it is poured into brine. The aqueous mixture is then extracted with ether and the ether solution is dried and concentrated. The residual material obtained is recrystallized from methanol to give 4,5β-epoxy-10-(2-propynyl)estrane-3,17-dione. This epoxide is added to 5 ml of acetic acid containing 0.1 ml of concentrated sulfuric acid and the mixture is stirred at 25° C. for 4 hours before it is poured into ice. The solid which forms is separated by filtration and recrystallized from ethyl acetate to give 4-hydroxy-10-(2-propynyl)estr-4-ene-3,17-dione. This compound has the following structural formula ##STR15##
Workup
- extractionThe aqueous mixture is then extracted with ether
- dry with materialthe ether solution is dried
- concentrationconcentrated
- customThe residual material obtained
- customis recrystallized from methanol
Sources & evidence
- ORD record
- ord-acd94ca6956647bfb79e71b2d167a837
- Source dataset
- uspto-grants-1982_03
- Patent number
- US04322416
Reaction notes
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