反应详情

To a stirred solution of mono-benzyl adipate (2.36 g, 10 mmol) in dry CH2Cl2 (50 ml) was added 5,5-dimethyl-1,3-cyclohexanedione (1.4 g, 10 mmol), N,N′-dicyclohexylcarbodiimide (2.1 g, 10.1 mmol) and 4-dimethylaminopyridine (1.22 g, 10 mmol). The resulting solution was allowed to stir at room temperature for 18 h. The solution was cooled and filtered to remove the precipitated N,N′-dicyclohexylurea. The filtrate was evaporated and the residue redissolved in EtOAc (50 ml) and washed with 1 M KHSO4. The organic extract was washed with brine (92×10 ml), dried (MgSO4) and evaporated to yield a white/yellow amorphous powder. Flash silica chromatography (EtOAc/hexane 1:2 v/v) afforded benzyl 6-hydroxy-6-(4,4-dimethyl-2,6-dioxocyclohexylidene)-hexanoate (3.00 g, 84%) as a white crystalline solid.

1. temperatureThe solution was cooled
2. filtrationfiltered
3. customto remove the precipitated N,N′-dicyclohexylurea
4. customThe filtrate was evaporated
5. dissolutionthe residue redissolved in EtOAc (50 ml)
6. washwashed with 1 M KHSO4
7. extractionThe organic extract
8. washwas washed with brine (92×10 ml)
9. dry with materialdried (MgSO4)
10. customevaporated
11. customto yield a white/yellow amorphous powder