Tetrabutylammonium Fluoride → HCID 58951441, compound

HRID 1445751Notes

Reaction equation

HRID 1445751 reaction equation
C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:6][CH2:7][CH2:8][C:9]1[N:10]=[C:11]([C:15]2[CH:28]=[CH:27][C:18]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)=[CH:17][CH:16]=2)[O:12][C:13]=1[CH3:14])(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:14][C:13]1[O:12][C:11]([C:15]2[CH:28]=[CH:27][C:18]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)=[CH:17][CH:16]=2)=[N:10][C:9]=1[CH2:8][CH2:7][OH:6]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58951494HCID 58951494, compound

Product 1

HCID 58951441HCID 58951441, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 2-(4-{4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-oxazol-2-yl}-phenoxymethyl)-pyridine (0.97 g, 1.76 mmol) in THF (20 mL) at 0° C. is added a solution of TBAF in THF (1.0 M, 1.76 mL). The mixture is warmed to room temperature and stirred for 2 h. The mixture is partitioned between EtOAc and water. The aqueous phase is extracted with EtOAc (3×). The combined organic phase is washed with brine (2×), dried (Na2SO4), and concentrated. The residue is purified by flash chromatography (SiO2, elute 0% to 10% MeOH/CH2Cl2) to yield 0.53 g of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 8.6 (dd, 1H), 7.8 (m, 3H), 7.6 (d, 1H), 7.4 (dd, 1H), 7.2 (d, 2H), 5.2 (s, 2H), 3.6 (t, 2H), 2.6 (t, 2H), 2.2 (s, 3H). MS (m/e) 311.1 (M+1)

Workup

  1. customThe mixture is partitioned between EtOAc and water
  2. extractionThe aqueous phase is extracted with EtOAc (3×)
  3. washThe combined organic phase is washed with brine (2×)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue is purified by flash chromatography (SiO2, elute 0% to 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-5bd1bc114739430faccfaf5e05e3f889
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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