Ammonium Chloride → HCID 19600247, compound

HRID 611405Notes

Reaction equation

HRID 611405 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:18])=[CH:15][CH:14]=3)(=[O:12])=[O:11])[CH2:5][C:4]=2[CH:3]=[CH:2]1.[Cl-].[NH4+]>O1CCCC1.C1([Mg]Br)C=CC=CC=1>[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]([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])[CH2:5][C:4]=2[CH:3]=[CH:2]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 19600233HCID 19600233, compound

Product 1

HCID 19600247HCID 19600247, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 178418255HCID 178418255, compoundSolvent

Procedure

To a solution of 0.252 g (0.865 mmol) of 4-(6,7-dihydro-4H-furo[3,2-c]pyridin-5-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 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-614236c1232f4749855a3d2d585fbe8e
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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