Tetrabutylammonium Fluoride → HCID 67777325, compound

HRID 1026356Notes

Reaction equation

HRID 1026356 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:31]=[CH:30][C:8]2[CH2:9][C:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][Si](C(C)C)(C(C)C)C(C)C)=[CH:15][N:14]=3)([CH3:12])[O:11][C:7]=2[CH:6]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:31]=[CH:30][C:8]2[CH2:9][C:10]([C:13]3[N:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=3)([CH3:12])[O:11][C:7]=2[CH:6]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67777888HCID 67777888, compound

Product 1

HCID 67777325HCID 67777325, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(6-(methoxymethoxy)-2-methyl-2,3-dihydrobenzofuran-2-yl)-5-(triisopropylsilyloxy)pyridine (8 g) and tetrabutylammonium fluoride (5.66 g) in THF (30 mL) was stirred at ambient temperature for 30 min. The mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane/methanol) to afford the title compound (4.66 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (dichloromethane/methanol)

Sources & evidence

ORD record
ord-3c8f3a6430284962b976e1ad14739d89
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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