(Diethylamino)sulfur trifluoride → HCID 86646156, compound
Reaction equation
O[CH2:2][CH2:3][CH:4]([CH2:12][CH:13]=[CH2:14])/[CH:5]=[CH:6]/[C:7]([O:9][CH2:10][CH3:11])=[O:8].CCN(S(F)(F)[F:21])CC.C(=O)(O)[O-].[Na+]>O1CCCC1>[F:21][CH2:2][CH2:3][CH:4]([CH2:12][CH:13]=[CH2:14])/[CH:5]=[CH:6]/[C:7]([O:9][CH2:10][CH3:11])=[O:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Ethyl(E)-4-(2-hydroxyethyl)-hepta-2,6-dienoate (5 g, 27.1 mmol) was dissolved in tetrahydrofuran (40 mL). To the solution, DAST (4.8 g, 29.8 mmol) was added under ice cooling, and the mixture was stirred for 1 hour. The reaction solution was poured to a saturated aqueous solution of sodium bicarbonate, followed by extraction with ethyl acetate. The ethyl acetate layer was washed with saturated saline, then dried, and then concentrated. The residue was purified by silica gel column chromatography (200 g) to obtain the compound of interest as an oil substance (2.2 g, 44%).