Hexamethylphosphoramide → 2-(5-Tetrahydropyranyloxy-3-pentynyl)cyclopropylmethyl t-butyldimethylsilyl ether

温度

0 °C

A tetrahydrofuran solution (15 ml) of propargyl alcohol tetrahydropyranyl ether (1.44 g, 10.3 mmol) was cooled to -78° C., and butyllithium (factor=1.5, 6.9 ml, 10.3 mmol) was added thereto. Fifteen minutes later, the temperature was raised to 0° C. Hexamethylphosphoric triamide (3.76 ml, 21 mmol) was added thereto, and the mixture was stirred for 15 minutes. A tetrahydrofuran solution of 2-(2-bromoethyl)cyclopropylmethyl t-butyldimethyl silyl ether (2.73 g, 10.3 mmol) was added thereto, and the mixture was stirred at room temperature for 2 hours. A saturated ammonium chloride solution was added thereto, and the product was extracted with ethyl ether. The crude product was purified by silica gel column chromatography to obtain 2-(5-tetrahydropyranyloxy-3-pentynyl)cyclopropylmethyl t-butyldimethylsilyl ether (3 g).

1. stirringthe mixture was stirred at room temperature for 2 hours
2. extractionthe product was extracted with ethyl ether
3. customThe crude product was purified by silica gel column chromatography

ORDレコード

ord-95a8518022b348ec9a34488da3a803fd

出典データセット

uspto-grants-1995_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05416231