Ethyl vinyl ether → HCID 68822771, compound

HRID 2378505Notes

Reaction equation

HRID 2378505 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]([O:21][CH2:22][CH3:23])=[CH2:20]>C1COCC1.FC(F)(F)C(O)=O>[CH2:19]([O:21][CH:22]([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)[CH3:23])[CH3:20]

Participants

5

Reactant 2

HCID 8023Ethyl vinyl etherHCID 67491946HCID 67491946, compound

Product 1

HCID 68822771HCID 68822771, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2 g (7.9 mmol) of (16) and 0.84 ml (8.7 mmol) ethyl vinyl ether in 2 ml THF was stirred at room temperature in the presence of 20 μl (0.32 mmol) trifluoroacetic acid for 2 days. After a short column filtration (SiO2) using diethyl ether as eluent and evaporation of the solvent 2.6 g of the crude product (18) was obtained. Flash chromatography, using SiO2 and cyclohexanelEtOAc=95:5 as eluent, afforded 2.10 g (82%) of (18) as a ˜1:1 mixture of diastereomers.

Workup

  1. filtrationAfter a short column filtration (SiO2)
  2. customevaporation of the solvent 2.6 g of the crude product (18)
  3. customwas obtained

Sources & evidence

ORD record
ord-a576a97b073a4cac935baf0f102016de
Source dataset
uspto-grants-2008_12
Patent number
US07470820B2

Reaction notes

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