Potassium Hydroxide → HCID 69625467, compound

HRID 1369374Notes

Reaction equation

[OH-].[K+].O.NN.[CH3:6][O:7][C:8]1([O:28][CH3:29])[CH2:25][CH2:24][C:23]2[C@@H:22]3[C@H:13]([C@H:14]4[C@@:18]([CH2:20][CH2:21]3)([CH3:19])[C:17](=O)[CH2:16][CH2:15]4)[C@H:12]([CH3:27])[CH2:11][C:10]=2[CH2:9]1>C(O)COCCO>[CH3:29][O:28][C:8]1([O:7][CH3:6])[CH2:25][CH2:24][C:23]2[C@@H:22]3[C@H:13]([C@H:14]4[C@@:18]([CH2:20][CH2:21]3)([CH3:19])[CH2:17][CH2:16][CH2:15]4)[C@H:12]([CH3:27])[CH2:11][C:10]=2[CH2:9]1

Participants

Conditions

Temperature: 130 °C

Procedure

Potassium hydroxide (1.5 g, 27 mmol) and hydrazine monohydrate (3 ml, 62 mmol) were added to a suspension of (7α)-3,3-dimethoxy-7-methylestr-5(10)-en-17-one (1 g, 3 mmol) in 17 mL diethyleneglycol at room temperature under a nitrogen atmosphere. The reaction mixture was heated for 1 hour at 130° C. followed by 1 hour and 15 minutes at 230° C. A Dean-Stark trap was used to remove the water and the excess of hydrazine. The reaction mixture was cooled down to room temperature and water was added and extracted with ethyl acetate. The organic layer was washed with brine, dried (Na2SO4) and evaporated to dryness to give the crude product (7α)-3,3-dimethoxy-7-methylestr-5(10)-ene, which was converted into (7α,16α,17β)-7,16-dimethyl-3-methylene-17-(1-propynyl)estr-5(10)-en-17-ol according to the procedures described above, mp 57° C.

Workup

customto remove the water
temperatureThe reaction mixture was cooled down to room temperature
additionwater was added
extractionextracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried (Na2SO4)
customevaporated to dryness

Sources & evidence

ORD record: ord-910223bd737545d8bcbe4537873426a7
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06579864B1

Reaction notes

Loading…