Water → HCID 53890816, compound

HRID 611413Notes

Reaction equation

HRID 611413 reaction equation
[O:1]1[C:9]2[CH2:8][CH2:7][N:6]([S:10]([C:13]3[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=3)(=[O:12])=[O:11])[CH2:5][C:4]=2[CH:3]=[CH:2]1.C[O-].[Na+].O>[Cl-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1.CO>[C:16]1([CH:17]=[CH:17][C:16]2[CH:19]=[CH:20][CH:13]=[CH:14][CH:15]=2)[CH:19]=[CH:20][C:13]([S:10]([N:6]2[CH2:7][CH2:8][C:9]3[O:1][CH:2]=[CH:3][C:4]=3[CH2:5]2)(=[O:12])=[O:11])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 19600233HCID 19600233, compound

Product 1

HCID 53890816HCID 53890816, compound

Reagents, catalysts & solvents 2

HCID 70671Benzyltriphenylphosphonium chlorideCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of 0.377 g (1.294 mmol) of 4-(6,7-dihydro-4H-furo[3,2-c]pyridin-5-ylsulfonyl)benzaldehyde and 0.60 g (1.55 mmol) of benzyltriphenylphosphonium chloride in 30 ml of methanol, 0.30 g (1.55 mmol) of 28% sodium methoxide in methanol was added dropwise at room temperature, followed by overnight stirring at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was subjected to silica gel column chromatography (hexane/ethyl acetate=3/1) to yield 5-(stilbene-4-sulfonyl)-4,5,6,7-tetrahydrofuro[3,2-c]pyridine as a mixture of the (E) and (Z)-isomers.

Workup

  1. extractionextracted with ethyl acetate 3 times
  2. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-84722a7c0be342a79ec58eaab20df4d8
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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