Hexane → HCID 68545185, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 17.15 g (46.7 mmol) of ((R)-1-benzenesulfonyl-3-methyl-hex-5-enyl)-carbamic acid tert-butyl ester in 100 ml dry THF under nitrogen atmosphere is cooled to −75° C. A solution A containing lithium furan-2-olate in THF is added over a period of 10 minutes via a canula using positive nitrogen pressure. Solution A is prepared as follows. A solution of 9.85 ml (46.7 mmol) HMDS in 100 ml dry THF under nitrogen atmosphere is cooled at −70° C. and 29.2 ml of a 1.6 M solution of BuLi in hexane (46.7 mmol) are added dropwise. After 30 minutes 3.92 g (46.7 mmol) 5H-furan-2-one in 2 ml dry THF are added dropwise and the temperature is kept at −40° C. After addition the reaction mixture is stirred at −75° C. for 1.5 h and then poured directly, with stirring, in 200 ml water and 200 ml EtOAc. The organic phase is washed successively with 5% aqueous citric acid, water (2×), 5% aqueous NaHCO3 solution and water (4×). The reaction mixture is evaporated and the residue chromatographed over silica gel (EtOAc/hexane 1:3) to yield the title compound as an oil.

Provenance & Evidence