Ethyl vinyl ether → HCID 68822419, compound

HRID 2378514Notes

Reaction equation

HRID 2378514 reaction equation
[OH:1][C:2]12[CH2:17][CH:16]([CH3:18])[CH2:15][C:14](=[O:19])[CH:13]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2.[CH:20]([O:22][CH2:23][CH3:24])=[CH2:21].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl.CCCCC.C(OCC)C>[CH2:20]([O:22][CH2:23][CH2:24][O:1][C:2]12[CH2:17][CH:16]([CH3:18])[CH2:15][C:14](=[O:19])[CH:13]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)[CH3:21]

Participants

6

Reactant 3

HCID 8023Ethyl vinyl etherHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 68826874HCID 68826874, compound

Product 1

HCID 68822419HCID 68822419, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21877078Diethylether pentaneSolvent

Procedure

A mixture of 133 mg (0.5 mmol) of (34) and 67 μl (0.7 mmol) ethyl vinyl ether in 0.4 ml CH2Cl2 was stirred at 40° C. in the presence of 63 mg (0.25 mmol) pyridinium p-toluenesulfonate (PPTS) for 3 hours (57% conversion). Flash chromatography of the reaction mixture, using SiO2 (14 g) and n-pentane/diethyl ether=9:1 as eluent, afforded 42 mg (25%) of (35) as a ˜1:1 mixture of diastereomers and 72 mg (0.27 mmol) of the starting material (34).

Sources & evidence

ORD record
ord-602202c7721a45e48436bef0a02b38ef
Source dataset
uspto-grants-2008_12
Patent number
US07470820B2

Reaction notes

Loading…