Methanol → 3,11alpha-Diacetoxy-estra-3,5-dien-17-one

HRID 1837271Notes

Reaction equation

[C:1]1([CH3:11])C=CC(S(O)(=O)=O)=CC=1.[OH:12][C@@H:13]1[CH2:30][C@@:28]2([CH3:29])[C@@H:24]([CH2:25][CH2:26][C:27]2=[O:31])[C@H:23]2[C@H:14]1[C@@H:15]1[C:20]([CH2:21][CH2:22]2)=[CH:19][C:18](=[O:32])[CH2:17][CH2:16]1.N1C=CC=CC=1.C[OH:40].[C:41](OC(=O)C)(=[O:43])[CH3:42]>>[C:41]([O:32][C:18]1[CH2:17][CH2:16][C@H:15]2[C:20](=[CH:21][CH2:22][C@@H:23]3[C@@H:14]2[C@H:13]([O:12][C:1](=[O:40])[CH3:11])[CH2:30][C@@:28]2([CH3:29])[C@H:24]3[CH2:25][CH2:26][C:27]2=[O:31])[CH:19]=1)(=[O:43])[CH3:42]

Participants

Reactant 5

HCID 887Methanol

HCID 1049Pyridine

HCID 6101p-Toluenesulfonic acid

HCID 7918Acetic Anhydride

HCID 1090229811a-Hydroxy-estr-4-ene-3,17-dione

Product 1

HCID 699180533,11alpha-Diacetoxy-estra-3,5-dien-17-one

Conditions

Temperature: -30 °C

Procedure

10 g of p-toluenesulfonic acid is added to 100 g of 11α-hydroxy-estr-4-ene-3,17-dione in 1 liter of acetic anhydride at room temperature. After 5 hours, the solution is stirred into pyridine-containing ice/water, the precipitated product is suctioned off and washed neutral with water. The water-moistened crude product that is obtained is mixed with 200 ml of methanol, stirred for 30 minutes at −30° C., the crystallizate is suctioned off, washed with cold methanol and dried in a vacuum at 50° C. 115 g of 3,11α-diacetoxy-estra-3,5-dien-17-one is obtained.

Workup

washwashed neutral with water
customThe water-moistened crude product that is obtained
washwashed with cold methanol
customdried in a vacuum at 50° C

Sources & evidence

ORD record: ord-cf1864457bfd4710a19fd493caf8dee8
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06780855B2

Reaction notes

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