Ethyl vinyl ether → HCID 68823891, compound

HRID 2378507Notes

Reaction equation

HRID 2378507 reaction equation
[OH:1][C:2]12[CH2:16][CH:15]([CH3:17])[CH2:14][C:13](=[O:18])[CH:12]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2.[CH:19](OCC)=[CH2:20].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[NH4+].[Cl-]>C1COCC1>[CH:19]([O:1][C:2]12[CH2:16][CH:15]([CH3:17])[CH2:14][C:13](=[O:18])[CH:12]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)=[CH2:20]

Participants

6

Reactant 4

HCID 8023Ethyl vinyl ether2×HCID 25517Ammonium ChlorideHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 67491946HCID 67491946, compound

Product 1

HCID 68823891HCID 68823891, compoundYield 19.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 1 g (4 mmol) of (16) and 0.46 ml (4.8 mmol) ethyl vinyl ether in 2 ml THF was stirred at room temperature in the presence of 201 mg (0.8 mmol) pyridinium p-toluenesulfonate (PPTS) for 4 hours. The mixture was stirred at 40° C. for 2 h and 0.46 ml (4.8 mmol) ethyl vinyl ether were added. After 6 hours at 40° C. the reaction the mixture was hydrolyzed with 3 ml of a saturated aqueous NH4Cl solution. After extraction with 50 ml diethyl ether the combined organic phases were washed (H2O), dried (Na2SO4) and the solvent was evaporated. Flash chromatography, using SiO2 (105 g) and n-pentane/diethyl ether=95:5 as eluent, afforded 215 mg (yield: 19%) of (26).

Workup

  1. customAfter 6 hours at 40° C. the reaction the mixture
  2. extractionAfter extraction with 50 ml diethyl ether the combined organic phases
  3. washwere washed (H2O)
  4. dry with materialdried (Na2SO4)
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-0870dd62ca75406399e14293c593e5b1
Source dataset
uspto-grants-2008_12
Patent number
US07470820B2

Reaction notes

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