反应详情

2.8 g. (8.2 mmoles) of 4,4-dimethyl-9-hydroxy-7-(3-methyl-2-octyl)-1,2,3,4-tetrahydrocyclopenta[ c][1]benzopyran, 1.77 g. (8.6 mmoles) of dicyclohexylcarbodiimide and 1.65 g. (8.5 mmoles) of β-piperidinopropionic acid hydrochloride (m.p. 216°-220°C., J. Am. Chem. Soc. 73, 3168 (1951) were combined with 125 ml. of methylene chloride and stirred at room temperature for about 20 hours. The reaction mixture was filtered and the methylene chloride removed using a rotary evaporator. The residue was treated with benzene and filtered to remove a small quantity of insoluble material. The benzene was evaporated and the dark, viscous residue was chromatographed using 100 g. of 60-100 mesh activated magnesium silicate (Florisil) and methanol/chloroform graded solvent mixtures. Chromatography gave a small quantity of orange oil which was dissolved in ether and treated with a solution of ethereal HCl. The desired compound appeared as white crystals which were filtered and washed with additional ether. The colorless crystals (86 mg., m.p. 106°-107°C.) were pure by thin layer chromatography (10% MeOH/CHCl3) and the nuclear magnetic resonance and infrared spectra were in agreement with the proposed structure.

1. filtrationThe reaction mixture was filtered
2. customthe methylene chloride removed
3. customa rotary evaporator
4. additionThe residue was treated with benzene
5. filtrationfiltered
6. customto remove a small quantity of insoluble material
7. customThe benzene was evaporated
8. customthe dark, viscous residue was chromatographed
9. customChromatography gave a small quantity of orange oil which