Dimethyl Carbonate → HCID 59835936、化合物

反応式

[S:1]1[C:5]2([CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]2)[S:4][CH2:3][CH2:2]1.[H-].[Na+].[C:14](=O)([O:17]C)[O:15][CH3:16]>C1COCC1>[CH3:16][O:15][C:14]([C:9]1[CH2:10][C:5]2([CH2:6][CH2:7][C:8]=1[OH:11])[S:4][CH2:3][CH2:2][S:1]2)=[O:17]

参加物

実験手順

To 1,4-dithia-spiro[4.5]decan-8-one (2.35 g, 12.5 mmoL, 1.0 eq), in THF (10 mL) at 0° C. under nitrogen was added NaH (60%, 2.0 g, 50 mmoL, 4.0 eq) slowly. After gas releasing was completed, dimethy carbonate (11.3 g, 125 mmoL, 10.0 eq) was added via syringe. The reaction mixture was warmed to room temperature and further heated at 50° C. for 2 hours. The reaction was then cooled down to room temperature and quenched with saturated ammonia chloride solution. The solvent was removed in vacuo and the residue was partitioned between ethyl ether and water. The aqueous layer was extracted with ethyl ether twice. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to give a colorless oil. The crude material was then purified by column chromatography using 5:1 hexanes: ethyl acetate to give the title compound as a colorless solid.