Benzene → (E)-ethyl 7-hydroxy-2-methyl-2-heptenate
Reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[OH:7].C([O:10][C:11]([CH2:13][CH:14]=[C:15]1CCP(C2C=CC=CC=2)C1(C1C=CC=CC=1)C1C=CC=CC=1)=O)C.[CH:38]1C=CC=CC=1>>[OH:10][CH2:11][CH2:13][CH2:14][CH2:15]/[CH:4]=[C:3](\[CH3:38])/[C:2]([O:1][CH2:6][CH3:5])=[O:7]Participants
4
Conditions
- Temperature
- 90 °C
Procedure
Tetrahydropyran-2-ol (2) (14.03 g; 0.138 mol) is added to a benzene solution (300 ml) of (ethoxycarbonylethylidene) triphenylphospholane (64.40 g; 0.178 mol) and the whole is refluxed at 90° C. for 1.5 hours. After the temperature is returned to room temperature, the solvent is then distilled off under reduced pressure, and the residue is separated and purified by column chromatography (developing solution, ethyl acetate:hexane=1:5) to produce Ester 3 (25.15 g; 0.135 mol) of 98% in yield.