Ethyl vinyl ether → HCID 19096758, compound

HRID 486966Notes

Reaction equation

HRID 486966 reaction equation
[C:1]1([CH:7]([NH:12][C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]([OH:11])[CH:9]=[CH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:21]([O:23][CH2:24][CH3:25])=[CH2:22].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>N1C=CC=CC=1.C(Cl)Cl>[C:1]1([CH:7]([NH:12][C:13](=[O:20])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:8]([O:11][CH:21]([O:23][CH2:24][CH3:25])[CH3:22])[CH:9]=[CH2:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 8023Ethyl vinyl etherHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 18462148HCID 18462148, compound

Product 1

HCID 19096758HCID 19096758, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

708 mg (2.65 mmol) of 1-phenyl-1-benzoylamino-2-hydroxybut-3-ene, syn form, 13.5 cm3 of dry methylene chloride, 2.53 cm3 (1.911 g, 26.5 mmol) of ethyl vinyl ether and 66.5 mg (0.265 mmol) of pyridinium p-toluenesulphonate (PPTS) are introduced successively into a 50 cm3 single-necked flask placed under an argon atmosphere and equipped with a magnetic stirring system. The resulting homogeneous reaction mixture is left to react for 4 hours at a temperature of about 20° C. When the reaction is complete, 1 drop of pyridine is added and the reaction mixture is then diluted in 20 cm3 of methylene chloride. The organic phase is washed once with 20 cm3 of water. The aqueous phase is extracted twice with 20 cm3 of methylene chloride. The combined organic phases are washed twice with 20 cm3 of water and once with 10 cm3 of a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulphate. After filtration, the solvents are driven off under reduced pressure on a rotary evaporator. The residue obtained (992 mg) is chromatographed on a column of silica gel. Elution with a hexane/ether mixture (6/4 by volume) gives 1-phenyl-1-benzoylamino-2-(1-ethoxyethoxy)but-3-ene, syn form, with a yield of 91% (818 mg, 2.41 mmol). The product obtained is in the form of an equimolar mixture of the two epimers (determination by the proton nuclear magnetic resonance spectrum).

Workup

  1. customequipped with a magnetic stirring system
  2. waitThe resulting homogeneous reaction mixture is left
  3. customto react for 4 hours at a temperature of about 20° C
  4. washThe organic phase is washed once with 20 cm3 of water
  5. extractionThe aqueous phase is extracted twice with 20 cm3 of methylene chloride
  6. washThe combined organic phases are washed twice with 20 cm3 of water and once with 10 cm3 of a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulphate
  8. filtrationAfter filtration
  9. customthe solvents are driven off under reduced pressure on a rotary evaporator
  10. customThe residue obtained (992 mg)
  11. customis chromatographed on a column of silica gel
  12. washElution with a hexane/ether mixture (6/4 by volume)

Sources & evidence

ORD record
ord-acf1efea1f4c4d39bc57e74230c7622c
Source dataset
uspto-grants-1994_03
Patent number
US05292921

Reaction notes

Loading…