Tetrabutylammonium Fluoride → HCID 70200053, compound

HRID 342471Notes

Reaction equation

HRID 342471 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:19][C:20]1[C:39]([O:40][Si](C(C)C)(C(C)C)C(C)C)=[CH:38][CH:37]=[C:36]([Cl:51])[C:21]=1[C:22]([NH:24][C:25]1[C:30]2[O:31][C:32]([CH3:35])=[C:33]([CH3:34])[C:29]=2[CH:28]=[CH:27][CH:26]=1)=[O:23]>O1CCCC1>[Cl:19][C:20]1[C:39]([OH:40])=[CH:38][CH:37]=[C:36]([Cl:51])[C:21]=1[C:22]([NH:24][C:25]1[C:30]2[O:31][C:32]([CH3:35])=[C:33]([CH3:34])[C:29]=2[CH:28]=[CH:27][CH:26]=1)=[O:23]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 70200654HCID 70200654, compound

Product 1

HCID 70200053HCID 70200053, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
4 °C

Procedure

A solution of tetrabutylammonium fluoride in tetrahydrofuran (1M solution, 0.58 ml) was added to a solution of 7-(2,6-dichloro-3-triisopropylsilyloxybenzoylamino)-2,3-dimethylbenzo[b]furan (221 mg) in tetrahydrofuran (2 ml) at 4° C. The solution was stirred at 4° C. for 1 hour and concentrated in vacuo. The residue was purified by column chromatography on silica gel and the obtained oil was crystallized from diisopropyl ether to give 7-(2,6-dichloro-3-hydroxybenzoylamino)-2,3-dimethylbenzo[b]furan (152 mg).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column chromatography on silica gel
  3. customthe obtained oil was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-f6e85122a2ee41e4b9898ed19c4b3d73
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

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