Réaction #74828

Équation de réaction

5-t-butoxycarbonyl-4-methoxycarbonylmethyl-5-(2-pentynyl)-2-cyclopentenone

5-tert-butoxycarbonyl-4-methoxycarbonylmethyl-5-(2-pentynyl)-2-cyclopentenone

compound ( 2-a )

5-tert-butoxycarbonyl-4-methoxycarbonylmethyl-5-(2-pentynyl)-2-cyclopentenone

lithium aluminum hydride

→

compound ( 1-a )

3-methoxycarbonylmethyl-2-t-butoxycarbonyl-2-(2-pentynyl)-cyclopentanol

Solvants

methanol

Conditions de réaction

Traitement

1. 1
   Températurethe solution is refluxed in a nitrogen atmosphere for one hour

Mode opératoire

A 5.5 g quantity of 5-t-butoxycarbonyl-4-methoxycarbonylmethyl-5-(2-pentynyl)-2-cyclopentenone (compound (2-a)) and 1.5 g of lithium aluminum hydride are dissolved in 200 ml of methanol, and the solution is refluxed in a nitrogen atmosphere for one hour. The same procedure as in Example 1 is thereafter followed, giving 3-methoxycarbonylmethyl-2-t-butoxycarbonyl-2-(2-pentynyl)-cyclopentanol (compound (1-a), R1 =t-butyl, R2 =CH3) in a yield of 93.4%, b.p. 80°-86° C./0.02 mm Hg.

Source