Sulfuric Acid → HCID 178448151, compound

HRID 372924Notes

Reaction equation

HRID 372924 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([CH:14]=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:16]([CH:19]([CH2:22]O)[CH2:20][OH:21])[CH2:17][CH3:18].S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[CH2:16]([C@@H:19]1[CH2:20][O:21][C@@H:14]([C:11]2[CH:10]=[CH:9][C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[N:13][CH:12]=2)[O:15][CH2:22]1)[CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 70211562-propylpropane-1,3-diolHCID 198125906-(4-Fluorophenyl)nicotinaldehyde

Product 1

HCID 178448151HCID 178448151, compoundYield 22.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1.51 g of 6-(4-fluorophenyl)-3-pyridinecarboxaldehyde and 1.10 g of 2-propyl-1,3-propanediol in 50 ml of toluene was treated with 10 drops of 10 percent (v/v) sulphuric acid. The mixture was heated to boiling for 1.5 hours, whereby moist toluene was distilled off and replaced by fresh toluene. Then, the reaction mixture was neutralized with triethylamine and, after cooling, washed three times with water, dried over sodium sulphate and concentrated. Chromatographic purification of the residue on 60 g of silica gel with toluene/acetone (vol. 99:1) and two-fold recrystallization of the trans/cis mixture from hexane/ethyl acetate (vol. 1:1) gave 0.51 g of pure 5-(trans-5-propyl-1,3-dioxan-2-yl)-2-(4-fluorophenyl)pyridine; m.p. (C-SA) 106.5° C., SA -N 117.5° C., cl.p. (N-I) 163° C.

Workup

  1. temperatureThe mixture was heated
  2. distillationwhereby moist toluene was distilled off
  3. temperatureafter cooling
  4. washwashed three times with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. customChromatographic purification of the residue on 60 g of silica gel
  8. customwith toluene/acetone (vol. 99:1) and two-fold recrystallization of the trans/cis mixture from hexane/ethyl acetate (vol. 1:1)

Sources & evidence

ORD record
ord-7871f92cb102441dba497f57a1bcb35c
Source dataset
uspto-grants-1992_11
Patent number
US05160661

Reaction notes

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