Imidazole → HCID 68970576, compound

Reaction equation

[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]

Participants

Procedure

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).