Formaldehyde → HCID 54278724, compound

HRID 274304Notes

Reaction equation

HRID 274304 reaction equation
[OH:1][C@@H:2]1[C@H:7]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C:4](=[O:22])[CH2:3]1)[C@:16]1([CH3:17])[C:11](=[CH:12][C:13](=[O:21])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3.[C:23]1([SH:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C=O.[CH3:32]CCCCC.C(OCC)(=O)C>N(CCO)(CCO)CCO>[OH:1][C@@H:2]1[C@H:7]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C:4](=[O:22])[CH2:3]1)[C@:16]1([CH3:17])[C:11](=[C:12]([CH2:32][S:29][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:13](=[O:21])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 7969ThiophenolHCID 1165238315alpha-Hydroxyandrost-4-ene-3,17-dioneHCID 21226206Ethyl acetate hexane

Product 1

HCID 54278724HCID 54278724, compound

Reagents, catalysts & solvents 1

HCID 7618TriethanolamineSolvent

Procedure

15 g of 15α-hydroxyandrost-4-ene-3,17-dione is reacted analogously to Example 6(a) with thiophenol and formaldehyde in triethanolamine. Chromatography of the crude product on silica gel with a hexane-ethyl acetate gradient yields 11 g of 15α-hydroxy-4-(phenylthiomethyl)androst-4-ene-3,17-dione as a foam.

Sources & evidence

ORD record
ord-67b12edc56e74af48a3a7e25056f902f
Source dataset
uspto-grants-1995_02
Patent number
US05389624

Reaction notes

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