2-Methoxymethylestradiol → 3-Hydroxy-2-methoxymethylestra-1,3,5(10)-trien-17-one

HRID 28339Notes

Reaction equation

[CH3:1][O:2][CH2:3][C:4]1[C:5]([OH:23])=[CH:6][C:7]2[CH2:8][CH2:9][C@@H:10]3[C@@H:19]([C:20]=2[CH:21]=1)[CH2:18][CH2:17][C@@:15]1([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]1[OH:22].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[OH:23][C:5]1[C:4]([CH2:3][O:2][CH3:1])=[CH:21][C:20]2[C@@H:19]3[C@H:10]([C@H:11]4[C@@:15]([CH2:17][CH2:18]3)([CH3:16])[C:14](=[O:22])[CH2:13][CH2:12]4)[CH2:9][CH2:8][C:7]=2[CH:6]=1

Participants

Conditions

Temperature: -70 °C

Procedure

262 mg (828 μmol) of 2-methoxymethyl-estra-1,3,5(10)-triene-3,17β-diol was dissolved in acetone, cooled to −70° C., and mixed in portions with Jones reagent (1.6 mmol). After 45 minutes, it was quenched with methanol, mixed with water and extracted with ethyl acetate. The combined organic phases were washed with a saturated sodium chloride solution, dried on sodium sulfate, and concentrated by evaporation in a rotary evaporator. Flash chromatography (n-hexane/ethyl acetate) yielded 97 mg (37%) of the desired product as colorless crystals.

Workup

customit was quenched with methanol
additionmixed with water
extractionextracted with ethyl acetate
washThe combined organic phases were washed with a saturated sodium chloride solution
customdried on sodium sulfate
concentrationconcentrated by evaporation in a rotary evaporator

Sources & evidence

ORD record: ord-973bdbdce5b74efa868db36615688a88
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07419972B2

Reaction notes

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