Methanol → 17-Hydroxy-16-methylidenepregn-4-ene-3,20-dione

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Reaction Steps

The crude 16-(phenylsulfinylmethyl)pregna-4,16-diene-3,20-dione (VIA, Example 38) is slurried in toluene (300 ml) under a nitrogen atmosphere. Methanol (2 mmole), triethylamine (0.13 mmole) and then trimethylphosphite (0.79 mmole) are added. The reaction mixture is sealed and heated under pressure at 90° for 4 hours, then cooled to 20°-25°. The reaction mixture is subjected to acid hydrolysis of the access trimethylphosphite, base and buffer washes and finally crystallization from toluene/heptane to give the title compound. NMR (CDCl3) 0.82, 1.20, 1.30, 3.5, 5.04, 5.21 and 5.68 δ

Provenance & Evidence