HCID 69069452, compound → HCID 69061805, compound
Reaction equation
[CH:1]1([CH2:4][CH:5]=[CH:6][CH2:7][CH2:8][CH:9]2[CH2:13][O:12]C(C)(C)[O:10]2)[CH2:3][CH2:2]1>CC(O)=O>[CH:1]1([CH2:4][CH:5]=[CH:6][CH2:7][CH2:8][CH:9]([OH:10])[CH2:13][OH:12])[CH2:2][CH2:3]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
Stirred 4-(5-Cyclopropyl-pent-3-enyl)-2,2-dimethyl-[1,3]dioxolane (0.30 g, 1.4 mmol) in 80% AcOH (5 mL) overnight at room temperature. Concentrated and purified by silica gel chromatography (70˜90% EtOAc in hexanes) to collect 7-Cyclopropyl-hept-5-ene-1,2-diol as a clear oil. 1H NMR (400 MHz, CDCl3): δ 5.52-5.47 (m, 1H), 5.41-5.35 (m, 1H), 3.77-3.71 (m, 1H), 3.66 (d, 1H, J=11.2 Hz), 3.46 (dd, 1H, J1=11.2 Hz, J2=7.7 Hz), 2.19-2.10 (m, 2H), 1.97 (t, 2H, J=7.1 Hz), 1.53-1.46 (m, 2H), 0.74-0.68 (m, 1H), 0.44-0.39 (m, 2H), 0.08-0.04(m, 2H).
Workup
- concentrationConcentrated
- custompurified by silica gel chromatography (70˜90% EtOAc in hexanes)