Imidazole → HCID 68970576、化合物

反応式

[OH:1][CH:2]1[CH:8]([OH:9])[C:7]2([CH3:11])[O:10][C:3]1([CH3:13])[CH2:4][C:5](=[O:12])[CH2:6]2.N1C=CN=C1.[C:19]([Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])(Cl)Cl)([CH3:22])([CH3:21])[CH3:20]>ClCCCl>[C:19]([Si:23]1([C:26]([CH3:29])([CH3:28])[CH3:27])[O:1][CH:2]2[CH:8]([C:7]3([CH3:11])[O:10][C:3]2([CH3:13])[CH2:4][C:5](=[O:12])[CH2:6]3)[O:9]1)([CH3:22])([CH3:21])[CH3:20]

参加物

実験手順

To a solution of 6,7-dihydroxy-1,5-dimethyl-8-oxa-bicyclo[3.2.1]octan-3-one (Bulletin of the Chemical Society of Japan (1983), 56(9), 2680-99, 550 mg, 2.95 mmol) in DCE (20 mL) was added imidazole (2.0 g, 29 mmol) and di-tert-butyldichlorosilane (1.2 mL, 5.9 mmol). The resulting mixture was stirred under Ar for 48 h. The reaction mixture was treated with satd. NaHCO3 (20 mL) and the DCE layer was separated, dried (Na2SO4) and concentrated and the residue obtained was purified on silica gel (5-20% EtOAc/hexane) to obtain the title compound (869 mg, 90%). 1H-NMR (CDCl3; 400 MHz): δ 4.23 (s, 2H), 2.43 (d, 1H, J=15.6 Hz), 2.31 (d, 1H, J=15.6 Hz), 1.45 (s, 6H), 1.12 (s, 9H), 1.04 (s, 9H).