반응 #1879360

반응 방정식

1α,3β-Bis(tert-butyldimethylsilyloxy)-17-(hydroxymethyl)androsta-5,7,16-triene

1-bromo-4-triethylsilyloxy-4-methyl-(2E)-pentene

sodium hydride

15-crown-5

→

titled compound

수율 100.0%

1α,3β-bis(tert-butyldimethylsilyloxy)-17-{4-triethylsilyloxy-4-methyl-(2E)-pentenyloxymethyl}androsta-5,7,16-triene

수율 100.0%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   기타of Example 5(1) (at room temperature for 2 hours)
2. 2
   기타purified by column chromatography (hexane:toluene=3:2)

실험 절차

1α,3β-Bis(tert-butyldimethylsilyloxy)-17-(hydroxymethyl)androsta-5,7,16-triene (400 mg, 0.734 mmol), 1-bromo-4-triethylsilyloxy-4-methyl-(2E)-pentene (431 mg, 1.47 mmol), sodium hydride (60% in oil, 88 mg, 2.20 mmol), 15-crown-5 (162 mg, 0.735 mmol) and tetrahydrofuran (1 ml) were subjected to reaction using a procedure similar to that of Example 5(1) (at room temperature for 2 hours), worked up and purified by column chromatography (hexane:toluene=3:2) to give the titled compound (556 mg, 100%) as a colorless oil.

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