Ammonium Chloride → HCID 19600213, compound

HRID 611398Notes

Reaction equation

HRID 611398 reaction equation
[O:1]1[C:5]2[CH2:6][N:7]([S:10]([C:13]3[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=3)(=[O:12])=[O:11])[CH2:8][CH2:9][C:4]=2[CH:3]=[CH:2]1.[Cl-].[NH4+]>O1CCCC1.C1([Mg]Br)C=CC=CC=1>[O:1]1[C:5]2[CH2:6][N:7]([S:10]([C:13]3[CH:20]=[CH:19][C:16]([CH:17]([C:13]4[CH:20]=[CH:19][CH:16]=[CH:15][CH:14]=4)[OH:18])=[CH:15][CH:14]=3)(=[O:12])=[O:11])[CH2:8][CH2:9][C:4]=2[CH:3]=[CH:2]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 19599952HCID 19599952, compound

Product 1

HCID 19600213HCID 19600213, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 178418255HCID 178418255, compoundSolvent

Procedure

To a solution of 0.142 g (0.487 mmol) of 4-(5,7-dihydro-4H-furo[2,3-c]pyridin-6-ylsulfonyl)benzaldehyde in 30 ml of tetrahydrofuran, phenylmagnesium bromide in tetrahydrofuran (prepared from 2.0 g of bromobenzene and 0.31 g of magnesium in 30 ml of tetrahydrofuran) was added at room temperature until the starting material disappeared on thin-layer chromatography (TLC). To the reaction mixture, aqueous ammonium chloride was added, followed by stirring and 3 extractions with ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 2/1) to yield the desired product.

Workup

  1. extraction3 extractions with ethyl acetate
  2. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 2/1)

Sources & evidence

ORD record
ord-4fb9e0a12338499997ac3c8ef051b736
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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