Tetrabutylammonium Fluoride → HCID 22291371, compound

HRID 967815Notes

Reaction equation

HRID 967815 reaction equation
[Si]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH:21]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:19]=[C:18]2[CH2:28][CH3:29])=[CH:13][CH:12]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:28]([C:18]1[N:17]([C:14]2[CH:13]=[CH:12][C:11]([CH2:10][CH2:9][OH:8])=[CH:16][CH:15]=2)[CH:21]=[C:20]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:19]=1)[CH3:29]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69693476HCID 69693476, compound

Product 1

HCID 22291371HCID 22291371, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-[4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)phenyl]-2-ethyl-4-phenyl-1H-imidazole (1.84 g, 4.6 mmol) in tetrahydrofuran (25 mL) was added tetrabutylammonium fluoride (1.84 g, 6.9 mmol) at 0° C. After 1 h, the reaction mixture was partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate and the combined organic phase was dried (MgSO4) and concentrated under reduced pressure. Purification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (gradient elution from 1:1 to 0:1) to afford 1.44 g (quant) of the title compound as colorless amorphous : MS (ESI) m/z 293 [M+H]+1H-NMR (CDCl3)δ1.26 (3H, t, J=7.5 Hz), 2.72 (2H, q, J=7.5 Hz), 2.95 (2H, t, J=6.6 Hz), 3.93 (2H, t, J=6.6 Hz), 7.22-7.28 (4H, m), 7.34-7.41 (4H, m), 7.79 (2H, d, J=7.1 Hz).

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and water
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. dry with materialthe combined organic phase was dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (gradient elution from 1:1 to 0:1)

Sources & evidence

ORD record
ord-8c602aea1e6a4f3087985e551dc18551
Source dataset
uspto-grants-2005_10
Patent number
US06956050B2

Reaction notes

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