Tetrahydrofuran → Acetone cyclohexane
Reaction equation
N[CH2:2]/[CH:3]=[CH:4]/[CH:5]=[CH2:6].[CH2:7]1[CH2:11][O:10]CC1>>[CH2:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:2][C:11]([CH3:7])=[O:10]Participants
Procedure
Initially introduce 83.2 g (1.0 mol) of (E)-1-amino-2,4-pentadiene (title compound from Example B.2.) in 250 ml of THF and add 0.1 g of 4-hydroxyanisole. Subsequently add dropwise 229.2 g (1.05 mol) of di-tert-butyl dicarbonate dissolved in 250 ml of THF at an internal temperature of 20°-30° C. After addition is complete stir at room temperature for 20 h. Add 103.0 g (1.05 mol) of maleic anhydride and heat to reflux for 5 h. Concentrate and take up the residue in 500 ml of methanol, add 30 ml of p-toluenesulphonic acid, then again heat to reflux for 5 h. After cooling, rapidly add dropwise a solution of 20 g of sodium carbonate dissolved in 500 ml of water with ice-cooling and stirring, allow mixture to stand for a further 30 min in the ice bath, filter off precipitate with suction, wash with a little water and dry to constant weight at 50° C.
Sources & evidence
- ORD record
- ord-0650bf1cec4e4a9e951be5388dcbff04
- Source dataset
- uspto-grants-1997_10
- Patent number
- US05679675
Reaction notes
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