p-Toluenesulfonic acid monohydrate → HCID 86751242, compound

HRID 1378268Notes

Reaction equation

HRID 1378268 reaction equation
[CH:1](/[CH:5]1[CH2:10][O:9][CH:8](CCCCC(CO)CO)[O:7][CH2:6]1)=[CH:2]\[CH2:3][CH3:4].FC1C=C(C=CC=1F)C=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH:1](/[CH:5]1[CH2:10][O:9][CH2:8][O:7][CH2:6]1)=[CH:2]\[CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 5880883,4-DifluorobenzaldehydeHCID 22910655HCID 22910655, compound

Product 1

HCID 86751242HCID 86751242, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 1.72 g of (E)-2-[4-(5-but-1-enyl-1,3-dioxan-2-yl)butyl]-1,3-propanediol and 1.0 g of 3,4-difluorobenzaldehyde in 30 ml of benzene is heated to slight boiling with 35 mg of p-toluenesulfonic acid monohydrate for 1 hour. After neutralization of the solution with a few drops of triethylamine the mixture is washed with water, dried over sodium sulfate, filtered and the filtrate is evaporated. The crude product is chromatographed on 40 g of silica gel with hexane/ethyl acetate 5% (v/v). Two-fold crystallization of the resulting isomer mixture from hexane yields pure (E)-trans-2-(3,4-difluorophenyl)-5-[4-(trans-5-but-1-enyl-1,3-dioxane.

Workup

  1. washAfter neutralization of the solution with a few drops of triethylamine the mixture is washed with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customthe filtrate is evaporated
  5. customThe crude product is chromatographed on 40 g of silica gel with hexane/ethyl acetate 5% (v/v)
  6. customTwo-fold crystallization of the resulting isomer mixture from hexane

Sources & evidence

ORD record
ord-60bde1b3bdfa47799f3244062297c660
Source dataset
uspto-grants-1997_09
Patent number
US05667721

Reaction notes

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