Iodic acid → HCID 21266601, compound
Reaction equation
[C:1]1([CH3:19])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[CH2:11][CH2:10][CH2:9]O1.[I:20](O)(=O)=O>>[C:1]1([CH3:19])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])=[CH:11][CH2:10][CH2:9][I:20]Participants
3
Procedure
A solution of 2,2-di-(2-tolyl)-tetrahydrofuran 33a (40 g) in 57% aqueous iodic acid (250 mL) was boiled under reflux for 30 min. The cooled solution was extracted with diethyl ether. The combined organic phases were washed with water and a saturated aqueous solution of NaCl, dried (Na2SO4) and evaporated in vacuo. The residue was subjected to CC (n-heptane/ethyl acetate 15:1) to give the title compound 36a as an oil (44 g). 1H NMR (CDCl3) 67 2.10 (s,3H), 2.30 (s,3H), 2.65 (q,2H), 3.19 (t,2H), 5.73 (t, 1H), 7.05-7.22 (m,8H)
Workup
- temperatureunder reflux for 30 min
- extractionThe cooled solution was extracted with diethyl ether
- washThe combined organic phases were washed with water
- dry with materiala saturated aqueous solution of NaCl, dried (Na2SO4)