Tetrabutylammonium Fluoride → HCID 18423644, compound

HRID 2270120Notes

Reaction equation

HRID 2270120 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Br:19][C:20]1[C:25]2[CH:26]=[C:27]([CH:29]3[CH2:33][CH2:32][O:31][CH2:30]3)[O:28][C:24]=2[C:23]([O:34][Si](C(C)(C)C)(C)C)=[CH:22][CH:21]=1>O1CCCC1>[Br:19][C:20]1[C:25]2[CH:26]=[C:27]([CH:29]3[CH2:33][CH2:32][O:31][CH2:30]3)[O:28][C:24]=2[C:23]([OH:34])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 18423646HCID 18423646, compound

Product 1

HCID 18423644HCID 18423644, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (8.1 ml, 1M in tetrahydrofuran) was added to a stirred solution of [4-bromo-2-(tetrahydrofuran-3-yl)-benzofuran-7-yloxy]-tert-butyldimethylsilane (2.69 g) in dry tetrahydrofuran (80 ml) at 0° C. under a dry nitrogen atmosphere. After stirring at this temperature for 45 minutes the solvent was removed in vacuo. The residue was partitioned between ethyl acetate (75 ml) and water (75 ml). The organic extract was dried over magnesium sulphate, filtered and concentrated in vacuo. Purification by column chromatography on silica eluting with 50% ethyl acetate in heptane afforded the title compound as a clear oil (1 g).

Workup

  1. customwas removed in vacuo
  2. customThe residue was partitioned between ethyl acetate (75 ml) and water (75 ml)
  3. extractionThe organic extract
  4. dry with materialwas dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by column chromatography on silica eluting with 50% ethyl acetate in heptane

Sources & evidence

ORD record
ord-35265ab064d342a6aeda7610e1539045
Source dataset
uspto-grants-2001_12
Patent number
US06331556B2

Reaction notes

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