Acetic Acid → Diisopropylether hexane

Participants

Reaction Steps

A mixture of 1,18 g of 1β-tert.-butoxy-8aβ-methyl-1,2,3,4,6,7,8,8a-octahydronaphthalene-6-one, 0,175 g of paraformaldehyde, 0.90 g of benzenesulfinic acid, 2,4 ml of N,N,N',N'-tetramethylethylendiamine and 1,6 ml of glacial acetic acid is stirred for 2 days at 70° under nitrogen atmosphere. The reaction mixture is taken up in chloroform, washed with a saturated solution of sodiumhydrogencarbonate and with 1 n HCl. The organic phase is dried with sodium sulfate and the solvent removed under vacuum. The yield of 2,33 g of the crude product is purified on silica gel by means of chromatography (benzine/ethyl acetate 95:5 → 50:50). After recristallisation from diisopropylether/hexane 0.452 g of rac. 1β-tert.-butoxy-8aβ-methyl-5-(phenylsulfonylmethyl)-1,2,3,4,6,7,8,8a-octahydronaphthalene-6-one is thus obtained, m.p. 96° - 98°. ε252 = 12700.

Provenance & Evidence