(Diethylamino)sulfur trifluoride → HCID 86646156, compound

HRID 551690Notes

Reaction equation

HRID 551690 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

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 86646155HCID 86646155, compound

Product 1

HCID 86646156HCID 86646156, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated saline
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (200 g)
  6. customto obtain the compound of interest as an oil substance (2.2 g, 44%)

Sources & evidence

ORD record
ord-1842d5e3a2244ce7a6e4fa78749afee2
Source dataset
uspto-grants-2011_05
Patent number
US07947738B2

Reaction notes

Loading…