Propiolic Acid → HCID 87566223, compound
Reaction equation
[CH2:1]([C:4]([F:22])([F:21])[C:5]([F:20])([F:19])[C:6]([F:18])([F:17])[C:7]([F:16])([F:15])[C:8]([F:14])([F:13])[C:9]([F:12])([F:11])[F:10])[CH2:2][OH:3].[C:23](O)(=[O:26])[C:24]#[CH:25].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:23]([O:3][CH2:2][CH2:1][C:4]([F:21])([F:22])[C:5]([F:19])([F:20])[C:6]([F:17])([F:18])[C:7]([F:15])([F:16])[C:8]([F:13])([F:14])[C:9]([F:12])([F:11])[F:10])(=[O:26])[C:24]#[CH:25]Participants
Conditions
- Temperature
- 0 °C
Procedure
1H,1H,2H,2H-perfluoro-1-octanol (10.1 g, 27.7 mmol) and propiolic acid (1.70 mL, 27.7 mmol) were dissolved in methylene chloride (15 mL), and the resulting solution cooled to 0° C. under nitrogen. To this was added a solution of dicyclohexylcarbodiimide (5.72 g, 27.7 mmol) and para-dimethylaminopyridine (0.034 g, 0.28 mmol) in methylene chloride (15 mL) over a 1 hour period, with stirring. The mixture was then allowed to warm to room temperature and a tan solid (dicyclohexylurea) precipitated. The reaction mixture was stirred overnight and then filtered to remove the dicyclohexylurea, and the filtrate was concentrated under vacuum to afford the crude product as a red oil. The crude product was chromatographed on a 15 cm×5 ccm silica gel column using 15% ethyl acetate in hexane to afford 8.31 g of (3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl) propiolate as a yellow oil (72% yield).
Workup
- temperatureto warm to room temperature
- customa tan solid (dicyclohexylurea) precipitated
- stirringThe reaction mixture was stirred overnight
- filtrationfiltered
- customto remove the dicyclohexylurea
- concentrationthe filtrate was concentrated under vacuum
- customto afford the crude product as a red oil
- customThe crude product was chromatographed on a 15 cm×5 ccm silica gel column
Sources & evidence
- ORD record
- ord-06622365389b49c9babcd864019056ba
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08309376B2
Reaction notes
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