Hepta-1,6-dien-4-ol → HCID 25137413, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium hydride (60% in mineral oil, 0.92 g, 23 mmol) in THF (10 mL), cooled to 0° C., 1,6-heptadien-4-ol 104 (1 mL, 7.7 mmol) was added dropwise in 10 sec. The resulting suspension was stirred at 0° C. for 30 min and then tert-butyldiphenylchlorosilane (2 mL, 7.9 mmol) was added. The reaction mixture was stirred at 23° C. for 4 h and then quenched with a saturated solution of ammonium chloride. The solvent was removed in vacuo and the aqueous phase was extracted with CH2Cl2. The organic extracts were dried (Na2SO4), the solvent was removed and the residue was purified by flash-chromatography (1:10 EtOAc/Hex) to afford 30 4-(tert-butyldiphenylsilyloxy)hepta-1,6-diene (2.6 g, 96%) as a colorless oil: δH (300 MHz, CDCl3) 7.70 (4H, dd, J1.6, 7.6 Hz, ArH), 7.47-7.38 (6H, m, ArH), 5.83-5.69 (2H, m, 2 CH═CH2), 5.02-4.91 (4H, m, 2.CH═CH2), 3.87-3.80 (1H, m, CHOSi), 2.31-2.12 (4H, m, 3-H2, 5-H2) and 1.08 [9H, s, 35 C(CH3)3]. To a solution of the above compound (2.0 g, 5.7 mmol) in dry CH2Cl2 (20 mL), second generation Grubbs catalyst (4.8 mg, 5.6 μmol) was added and the resulting mixture was heated under reflux for 2 h. Subsequently, the reaction mixture was cooled to 23° C., the solvent was 40 removed under reduced pressure and the residue was purified by flash-chromatography (1:10 EtOAc/Hex) to afford 105 (1.8 g, 98%) as a colorless oil: δH (300 MHz, CDCl3) 7.67 (4H, dd, J1.8, 7.8, ArH), 7.45-7.34 (6H, m, ArH), 5.61 (2 H, s, 1-H, 2-H), 4.57-4.51 (1H, m, 4-H), 2.47-2.33 (4H, m, 3-H2, 5-H2) 45 and 1.05 [9H, s, C(CH3)3].

Provenance & Evidence