تفاعل #2390634

معادلة التفاعل

3,3a,6,6a-tetrahydro-cyclopenta[b]furan-2-one

lithium bis-(trimethylsilyl)-amide

2-(bromomethyl)-naphthalene

→

title compound

3-(Naphth-2-ylmethyl)- 3,3a,6,6a-tetrahydro-cyclopenta[b]furan-2-one

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىChromatographic purification
2. 2
   workup.ADDITIONa mixture of dichloromethane and petroleum ether (40-60) in a ratio of 100:4

الإجراء التجريبي

Analogously to the procedure of Example 1, the title compound was prepared from 7.4 g (59.6 mmol) of 3,3a,6,6a-tetrahydro-cyclopenta[b]furan-2-one, 60 ml of a 1 molar lithium bis-(trimethylsilyl)-amide solution in THF and 13.2 g (59.7 mmol) of 2-(bromomethyl)-naphthalene in 180 ml of THF. Chromatographic purification is carried out using a mixture of dichloromethane and petroleum ether (40-60) in a ratio of 100:4. Yield: 10.6 g (67.3%), pale yellow oil, diastereomeric mixture: 2.5:1 (Example 7). MS (ESI)[m/e]: 287 [M+Na+]

المصدر