Methanol → HCID 19019154, compound
Reaction equation
[Br:1][CH2:2][CH2:3][CH:4]1[O:8][C:7](C)(C)[O:6][C:5]1=[O:11].CC1C=CC(S(O)(=O)=O)=CC=1.O.CO>C1(C)C=CC=CC=1>[CH3:7][O:6][C:5](=[O:11])[CH:4]([OH:8])[CH2:3][CH2:2][Br:1]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 5-(2-bromo-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-one (synthesized as instructed in Tetrahedron Letters, 1997, 38, 28, 4935) (93 mg, 0.416 mmol) in toluene (0.5 mL) were added p-TsOH.H2O (8 mg, 0.0415 mmol) and methanol (0.5 mL), followed stirring overnight at room temperature. The solution was concentrated in a vacuum, diluted with dichloromethane and washed with an aqueous saturated sodium bicarbonate solution. The organic layer thus formed was dried over sodium sulfate and filtered. The filtrate was concentrated to produce 68 mg of the compound as an oil. 1H NMR (300 MHz, CDCl3) δ 1.98 (1H, m), 2.34 (1H, m), 2.96 (1H, d), 3.56 (2H, m), 3.82 (3H, s), 4.37 (1H, pentet).