Hydrochloric Acid → 2-Methoxyestra-1,3,5(10)-triene-3-ol

HRID 1781989

Reaction equation

[CH3:1][C@@:2]12[C:18](=O)[CH2:17][CH2:16][C@H:15]1[C@H:14]1[C@@H:5]([C:6]3[C:11]([CH2:12][CH2:13]1)=[CH:10][C:9]([OH:20])=[C:8]([O:21][CH3:22])[CH:7]=3)[CH2:4][CH2:3]2.O.NN.[OH-].[K+].Cl>C(O)CO.C(O)CCC>[CH3:22][O:21][C:8]1[C:9]([OH:20])=[CH:10][C:11]2[CH2:12][CH2:13][C@@H:14]3[C@@H:5]([C:6]=2[CH:7]=1)[CH2:4][CH2:3][C@@:2]1([CH3:1])[C@H:15]3[CH2:16][CH2:17][CH2:18]1

Participants

Conditions

Temperature: 130 °C

Procedure

2-Methoxyestrone (Scheme 1, Compound 4) (450 mg, 1.5 mmol) was suspended in ethylene glycol (10 mL) and n-butanol (2 mL). Hydrazine hydrate (0.145 mL, 3 mmol) was added and the mixture was heated to 130° C. for 1 h. The reaction was cooled to 70° C., KOH (253 mg, 4.5 mmol) was added, then the reaction was heated at 200° C. for 1 h. The mixture was cooled to room temperature, poured into ice and HCl (6N, 6 mL) was added. The resulting solid was filtered off. The solid was dissolved in acetone, which was then evaporated to give a product (Scheme 1, Compound 7) (310 mg, 72% yield). 1H NMR (300 MHz, CDCl3) δ 6.93 (1H, s, aromatic), 6.75 (1H, s, aromatic), 5.35 (1H, s, phenol), 3.95 (3H, s, methoxy), 2.95 (2H, dd, J=5.0, 3.0 Hz), 2.25 (2H, m,), 1.95 (2H, m), 1.95-1.05 (11H, m), 0.8 (3H, s)

Workup

temperatureThe reaction was cooled to 70° C.
temperaturethe reaction was heated at 200° C. for 1 h
temperatureThe mixture was cooled to room temperature
additionwas added
filtrationThe resulting solid was filtered off
dissolutionThe solid was dissolved in acetone
customwhich was then evaporated

Sources & evidence

ORD record: ord-b3178f60b4774d0b9e3efc65f3fe44ff
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07498322B2

Linked notes

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