Water → FR167356

HRID 342452Notes

Reaction equation

HRID 342452 reaction equation
[C:1]([C:4]1[C:5]2[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C:15](=[O:24])[C:16]3[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:23])[C:6]=2[O:7][C:8]=1[CH3:9])(=[O:3])[CH3:2].[CH3:25][Mg]Br.[Cl-].[NH4+].O>O1CCCC1>[Cl:22][C:21]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:23])[C:16]=1[C:15]([NH:14][C:10]1[C:6]2[O:7][C:8]([CH3:9])=[C:4]([C:1]([OH:3])([CH3:25])[CH3:2])[C:5]=2[CH:13]=[CH:12][CH:11]=1)=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 70199583HCID 70199583, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 10068207FR167356

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-acetyl-7-(2,6-dichlorobenzoylamino)-2-methylbenzo[b]furan (100 mg) in tetrahydrofuran (3 ml) was added a 1M solution of methylmagnesium bromide in tetrahydrofuran (0.7 ml) dropwise with ice cooling. The solution was stirred at ambient temperature for 2 hours and to the solution was added aqueous saturated ammonium chloride. Then, the mixture was poured into water and the separated oil was extracted with ethyl acetate. The extract was washed with brine, dried over sodium sulfate and evaporated in vacuo. The residue was purified by colimn chromatography on silica gel and the obtained oil was crystallized from a mixture of diisopropyl ether and hexane to give 7-(2,6-dichlorobenzoylamino)-3-(1-hydroxy-1-methylethyl)-2-methylbenzo[b]furan (75 mg).

Workup

  1. extractionthe separated oil was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by colimn chromatography on silica gel
  6. customthe obtained oil was crystallized from a mixture of diisopropyl ether and hexane

Sources & evidence

ORD record
ord-251709e8a61e44c3b13b7b6e12aef3db
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

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