1,3-Propanediol → 1-(3-(1,3-Dioxan-2-yl)phenyl)-5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazole

HRID 2196563Notes

Reaction equation

HRID 2196563 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=2)[CH:14]=[O:15])[N:9]=[C:8]([C:19]([F:22])([F:21])[F:20])[CH:7]=1.[CH2:23](O)[CH2:24][CH2:25][OH:26].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:15]1[CH2:23][CH2:24][CH2:25][O:26][CH:14]1[C:13]1[CH:12]=[C:11]([N:10]2[C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)=[CH:7][C:8]([C:19]([F:20])([F:22])[F:21])=[N:9]2)[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 104421,3-PropanediolHCID 521998p-Toluenesulfonic acid monohydrateHCID 598432493-(5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzaldehyde

Product 1

HCID 598432051-(3-(1,3-Dioxan-2-yl)phenyl)-5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazoleYield 79%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 122 (3.25 g, 10.62 mmol) in PhMe (53 ml) was added 1,3-propanediol (1.616 g, 21.24 mmol) followed by p-toluenesulfonic acid monohydrate (0.202 g, 1.062 mmol) and the resulting solution was allowed to stir at reflux with a Dean-Stark trap for 16 h. The solution was evaporated to dryness, and saturated NaHCO3 aqueous solution was added and the mixture was extracted with EtOAc and the extracts were dried over Na2SO4 and evaporated. The residue was purified via Biotage (5% to 40% EtOAc/Hexane; 40+M column). The title product 146 (3.04 g, 8.34 mmol, 79% yield) was obtained as an off-white solid. LRMS (ESI): (calc.) 364.3; (found) 365.2 (MH)+.

Workup

  1. temperatureat reflux with a Dean-Stark trap for 16 h
  2. customThe solution was evaporated to dryness, and saturated NaHCO3 aqueous solution
  3. additionwas added
  4. extractionthe mixture was extracted with EtOAc
  5. dry with materialthe extracts were dried over Na2SO4
  6. customevaporated
  7. customThe residue was purified via Biotage (5% to 40% EtOAc/Hexane; 40+M column)

Sources & evidence

ORD record
ord-57df07ce7a67448484a6d13b37f24768
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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