HCID 22822149, compound → HCID 54383316, compound

HRID 2199093Notes

Reaction equation

[OH:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2(SC)[S:20][CH3:21])[C@H:12]2[C@H:3]1[C@:4]1([CH3:25])[C:9]([CH2:10][CH2:11]2)=[CH:8][C:7](=[O:24])[CH:6]=[CH:5]1>C(C1C=CC=CC=1CC)C>[OH:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH:15]=[C:16]2[S:20][CH3:21])[C@H:12]2[C@H:3]1[C@:4]1([CH3:25])[C:9]([CH2:10][CH2:11]2)=[CH:8][C:7](=[O:24])[CH:6]=[CH:5]1

Participants

Conditions

Temperature: 200 °C

Procedure

A suspension of 11β-hydroxy-17,17-bis-(methylthio)androsta-1,4-diene-3-one (2.6 g) in dry diethylbenzene (120 ml) is refluxed for 1.0 hour in a bath at about 200° C. The resulting solution is then cooled to room temperature and subsequently in an ice bath to afford the title compound as needles (2.1 g), after filtration and washing with hexane. The filtrate is subsequently chromatographed on a column of silica gel (30 g) to afford another 100 mg of product. The total yield is thus 2.2 g of product, melting point 240°-241° C., dec., with a consistent nmr spectrum.

Workup

temperatureThe resulting solution is then cooled to room temperature and subsequently in an ice bath

Sources & evidence

ORD record: ord-f4de5ee1862b463da5529745e2a17356
Source dataset: uspto-grants-1982_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04361559

Reaction notes

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