m-Chloroperbenzoic acid → HCID 18638782, compound

HRID 1649714Notes

Reaction equation

ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]1[O:35][C:15]2([CH2:32][CH2:31][C:30]3[C:29]4[C@H:20]([C@H:21]5[C@@:25]([CH2:27][CH:28]=4)([CH3:26])[C@@H:24]([OH:33])[CH2:23][CH2:22]5)[C@@H:19]([CH3:34])[CH2:18][C:17]=3[CH2:16]2)[O:14][CH2:13]1>C(Cl)Cl.C(=O)([O-])O.[Na+]>[CH2:13]1[O:14][C:15]2([CH2:32][CH2:31][C@:30]34[O:9][C@:17]3([CH2:18][C@H:19]([CH3:34])[C@@H:20]3[C:29]4=[CH:28][CH2:27][C@@:25]4([CH3:26])[C@H:21]3[CH2:22][CH2:23][C@@H:24]4[OH:33])[CH2:16]2)[O:35][CH2:12]1

Participants

Conditions

Temperature: -35 °C

Procedure

11.6 g of solid sodium hydrogen carbonate and 15.8 g of m-chloroperbenzoic acid were added consecutively scoopwise at -35° C. to a cooled solution of 22 g of 17β-hydroxy-7β-methyloestr-5(10),9(11)-dien-3-one-3-ethyleneacetal in 350 ml of methylene dichloride. After being stirred for 1 hour at -35° C., the reaction mixture was diluted with a saturated sodium hydrogen carbonate solution followed by extraction with methylene dichloride. The organic layer was washed with 0.2M sulphite solution and with water until neutral, dried on sodium sulphate, filtered and evaporated to dryness in vacuo. After purification by chromatography through silica gel, 8.8 g of 5α,10α-epoxy-17β-hydroxy-7β-methyloestr-9(11)-en-3-one-3-ethyleneacetal were obtained.

Workup

extractionfollowed by extraction with methylene dichloride
washThe organic layer was washed with 0.2M sulphite solution and with water until neutral,
customdried on sodium sulphate
filtrationfiltered
customevaporated to dryness in vacuo
customAfter purification by chromatography through silica gel

Sources & evidence

ORD record: ord-14d6d33df8c542b89fecfab7c2fbd811
Source dataset: uspto-grants-1990_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04921845

Reaction notes

Loading…