Ethyl vinyl ether → HCID 68823436, compound

HRID 2378512Notes

Reaction equation

HRID 2378512 reaction equation
[OH:1][C:2]12[CH2:15][CH:14]([CH3:16])[CH2:13][C:12](=[O:17])[CH:11]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2.[CH:18]([O:20][CH2:21][CH3:22])=[CH2:19].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CCCCC.C(OCC)C>[CH2:18]([O:20][CH:21]([O:1][C:2]12[CH2:15][CH:14]([CH3:16])[CH2:13][C:12](=[O:17])[CH:11]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)[CH3:22])[CH3:19]

Participants

5

Reactant 3

HCID 8023Ethyl vinyl etherHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 67260803HCID 67260803, compound

Product 1

HCID 68823436HCID 68823436, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 21877078Diethylether pentaneSolvent

Procedure

A mixture of 119 mg (0.5 mmol) of (30) and 384 μl (4 mmol) ethyl vinyl ether was stirred at 25° C. in the presence of 25 mg (0.1 mmol) pyridinium p-toluenesulfonate (PPTS) for 2 hours (94% conversion). Flash chromatography of the reaction mixture, using SiO2 (14 g) and n-pentane/diethyl ether=95:5 as eluent, afforded 105 mg (61%) of (31) as a ˜1:1 mixture of diastereomers.

Sources & evidence

ORD record
ord-86a4bb1e831449798c783df0975a4cb6
Source dataset
uspto-grants-2008_12
Patent number
US07470820B2

Reaction notes

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