Perfluoropentanoic acid → HCID 86759615, compound

HRID 984302

Reaction equation

HRID 984302 reaction equation
[O:1]1[CH:6]([CH2:7][OH:8])[CH2:5][O:4][C:3]2=[CH:9][S:10][CH:11]=[C:2]12.[F:12][C:13]([F:27])([C:17]([F:26])([F:25])[C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20])[C:14](O)=[O:15].CCN=C=NCCC[N+](C)(C)C.[I-].CNC1C=NC=CC=1NC>ClCCl>[O:1]1[CH:6]([CH2:7][O:8][C:14](=[O:15])[C:13]([F:12])([F:27])[C:17]([F:25])([F:26])[C:18]([F:23])([F:24])[C:19]([F:22])([F:21])[F:20])[CH2:5][O:4][C:3]2=[CH:9][S:10][CH:11]=[C:2]12

Participants

6

Reactant 4

HCID 75921Perfluoropentanoic acidHCID 1222421-(3-(Dimethylamino)propyl)-3-ethylcarbodiimide methiodideHCID 160674382,3-Dihydrothieno(3,4-b)-1,4-dioxin-2-methanolHCID 54034249HCID 54034249, compound

Product 1

HCID 86759615HCID 86759615, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2,3-Dihydro-thieno[3,4-b][1,4]dioxin-2-yl)-methanol (“hydroxymethyl EDOT”, 1.20 g, 6.97 mmol) in dichloromethane (30 mL) was chilled to 0° C. under argon. Neat 2,2,3,3,4,4,5,5,5-nonafluoropentanoic acid (1.93 g, 7.35 mmol) was added by pipette. Quickly 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide methiodide (2.30 g, 7.80 mmol) and 3,4-dimethylaminopyridine (0.1 g, 0.82 mmol) were added and the solution was allowed to come to room temperature overnight. The solvent was evaporated at <30° C. and the residue purified by repeated column chromatography on silica gel using a gradient elution starting with 3:1 hexane/dichloromethane and ending with 1:1 hexane/dichloromethane. The product (2.10 g, 5.02 mmol) was a colorless oil that solidifies at −20° C. (Formula (4), left-hand side). Overall product yield was 53%.

Workup

  1. customThe solvent was evaporated at <30° C.
  2. customthe residue purified
  3. washa gradient elution
  4. customthat solidifies at −20° C.

Sources & evidence

ORD record
ord-53190ed3f29846dbb93c93721d84192b
Source dataset
uspto-grants-2005_03
Patent number
US06867281B2

Linked notes

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