Formaldehyde → HCID 15679150, compound

HRID 2254630Notes

Reaction equation

HRID 2254630 reaction equation
[OH:1][C@@:2]1([CH3:23])[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C:11](=[CH:12][C:13](=[O:21])[CH2:14][CH2:15]1)[C:10](=[CH2:22])[CH2:9]3.[C:24]1([SH:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C=O.[CH3:33]CCCCC.C(OCC)(=O)C>N(CCO)(CCO)CCO>[OH:1][C@@:2]1([CH3:23])[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C:11](=[C:12]([CH2:33][S:30][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:13](=[O:21])[CH2:14][CH2:15]1)[C:10](=[CH2:22])[CH2:9]3

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 7969ThiophenolHCID 12951792HCID 12951792, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 15679150HCID 15679150, compound

Reagents, catalysts & solvents 1

HCID 7618TriethanolamineSolvent

Procedure

Analogously to Example 6(a), 200 mg of 17β-hydroxy-17α-methyl-6-methyleneandrost-4-en-3-one (Tetrahedron 20: 597, 1964) is reacted with thiophenol and formaldehyde in triethanolamine. After chromatography of the crude product on silica gel with a hexane-ethyl acetate gradient, 190 mg of 17β-hydroxy-17α-methyl-6-methylene-4-(phenylthiomethyl)androst-4-en-3-one is obtained as an oil.

Sources & evidence

ORD record
ord-64beff46361e4cd7b3e6a6be5235a83e
Source dataset
uspto-grants-1993_08
Patent number
US05236912

Reaction notes

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