Ethyl vinyl ether → HCID 19737970, compound

HRID 2255507Notes

Reaction equation

HRID 2255507 reaction equation
[CH2:1]([N:4]1[CH2:9][CH:8]([OH:10])[C:7]2[CH:11]=[CH:12][S:13][C:6]=2[S:5]1(=[O:15])=[O:14])[CH:2]=[CH2:3].[CH2:16]([O:18][CH:19]=[CH2:20])[CH3:17]>O1CCCC1.C(OCC)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:1]([N:4]1[CH2:9][CH:8]([O:10][CH2:17][CH2:16][O:18][CH2:19][CH3:20])[C:7]2[CH:11]=[CH:12][S:13][C:6]=2[S:5]1(=[O:15])=[O:14])[CH:2]=[CH2:3]

Participants

6

Reactant 2

HCID 8023Ethyl vinyl etherHCID 19737997HCID 19737997, compound

Product 1

HCID 19737970HCID 19737970, compoundYield 95.8%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

The product from Step A (4.2 g, 17.1 mmol) was dissolved in tetrahydrofuran (75 mL) and cooled to 0° C. at which point p-toluenesulfonic acid (163 mg, 0.6 mmol) was added followed by ethylvinyl ether (3.3 mL, 34.3 mmol). This mixture was stirred at 0° C. for 2 h, diluted with cold ethyl acetate (100 mL) and washed with saturated sodium bicarbonate (70 mL) and brine (70 mL). The organic layer was dried (MgSO4) and evaporated to provide 5.2 g of crude product which was used in the next step without further purification.

Workup

  1. additionwas added
  2. washwashed with saturated sodium bicarbonate (70 mL) and brine (70 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-6fe85561ab3b4be08d0bfb56414c76ec
Source dataset
uspto-grants-1993_08
Patent number
US05240923

Reaction notes

Loading…