p-Toluenesulfonic acid → HCID 57175086, compound

HRID 2254465Notes

Reaction equation

HRID 2254465 reaction equation
[Br-].[CH3:2][O:3][CH:4]([O:31][CH3:32])[C:5]1[CH:6]=[C:7]([CH:28]=[CH:29][CH:30]=1)[CH2:8][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.OCC1C=C(C=CC=1)C=O.P(Br)(Br)Br.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:77]1([C:82]2[CH:83]=[C:84]([CH:87]=[CH:88][CH:89]=2)[CH:85]=O)[CH:81]=[CH:80][CH:79]=[CH:78]1.C[O-].[Na+]>CO>[CH3:32][O:31][CH:4]([O:3][CH3:2])[C:5]1[CH:30]=[CH:29][CH:28]=[C:7]([CH:8]=[CH:85][C:84]2[CH:87]=[CH:88][CH:89]=[C:82]([N:77]3[CH:81]=[CH:80][CH:79]=[CH:78]3)[CH:83]=2)[CH:6]=1

Participants

9

Reactant 7

HCID 6101p-Toluenesulfonic acidHCID 11776TriphenylphosphineHCID 24614Phosphorus tribromideHCID 27765283-(1H-Pyrrol-1-yl)benzaldehydeHCID 10942334Sodium MethoxideHCID 131314553-(Hydroxymethyl)benzaldehydeHCID 19744548HCID 19744548, compound

Product 1

HCID 57175086HCID 57175086, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

560 mg of 3-(dimethoxymethyl)benzyltriphenylphosphonium bromide synthesized by brominating 3-hydroxymethylbenzaldehyde with phosphorus tribromide, and then acetalizing the product in anhydrous methanol in the presence of p-toluenesulfonic acid, followed by reacting it with triphenylphosphine] and 180 mg of 3-(1-pyrrolyl)benzaldehyde [synthesized by oxidizing 3-(1-pyrrolyl)benzyl alcohol with pyridinium chlorochromate in chloroform]were dissolved in 20 ml of methanol. 110 mg of sodium methoxide was added, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, and ethyl acetate and water were added to the residue to extract it. The organic layer was worked up in a customary manner, and purified by medium-pressure liquid chromatography [Lobar column, size B, Lichroprep Si 60 (E. Merck Co.); eluting solvent: hexane/ethyl acetate=10/1] to give 135 mg (yield 42%) of an E-form of 3-[2-[3-(1-pyrrolyl)phenyl]ethenyl]benzaldehyde dimethyl acetal and 127 mg of its Z-form.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and ethyl acetate and water
  2. additionwere added to the residue
  3. extractionto extract it
  4. custompurified by medium-pressure liquid chromatography [Lobar column, size B, Lichroprep Si 60 (E. Merck Co.); eluting solvent: hexane/ethyl acetate=10/1]

Sources & evidence

ORD record
ord-6033ddb052ba42c2a18642fc1e7ad741
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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