Propanal → HCID 21478983, compound

HRID 2292660Notes

Reaction equation

HRID 2292660 reaction equation
[OH:1][CH:2]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[CH:18]=[CH:17][CH:16]=[N:15]2)=[CH:9][CH:8]=1)CO.[CH:19](=[O:22])[CH2:20][CH3:21].[C:23]1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[N:14]1([CH2:13][C:10]2[CH:9]=[CH:8][C:7]([O:6][CH:5]3[CH2:2][O:1][C:19]([CH3:23])([CH2:20][CH3:21])[O:22]3)=[CH:12][CH:11]=2)[CH:18]=[CH:17][CH:16]=[N:15]1

Participants

6

Reactant 4

HCID 527PropanalHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 21478985HCID 21478985, compound

Product 1

HCID 21478983HCID 21478983, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of this 2-hydroxy-3-[4-(1-pyrazolyl)methylphenoxy]propanol (941 mg), propionaldehyde (308 mg), dry toluene (20 ml) and a catalytic amount of p-toluenesulfonic acid was heated at reflux under stirring for 4 hours. Then, the reaction mixture was poured into ice-cooled 5% aqueous sodium hydrogencarbonate (100 ml), followed by two extractions with ethyl acetate (50 ml). The organic layers were combined, washed with saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, which afforded 723 mg of 4-[4-(1-pyrazolyl)methylphenoxy]-methyl-2-ethyl-1,3-dioxolane (compound 38). Yield, 66% (based upon 2-hydroxy-3-[4-(1-pyrazolyl)methylphenoxy]propanol).

Workup

  1. temperatureat reflux
  2. additionThen, the reaction mixture was poured into ice-
  3. extractionfollowed by two extractions with ethyl acetate (50 ml)
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-86680b9dddac4470970a7cb2f2de29c7
Source dataset
uspto-grants-1997_11
Patent number
US05684022

Reaction notes

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