Tetrahydrofuran → HCID 4001499, compound

HRID 2167325Notes

Reaction equation

HRID 2167325 reaction equation
F[C:2]1[CH:11]=[CH:10][C:5]([C:6](=[N:8][OH:9])[NH2:7])=[CH:4][CH:3]=1.[F-:12].C([N+]([CH2:26][CH2:27][CH2:28][CH3:29])(CCCC)CCCC)CCC.[CH2:30]1[CH2:34]OC[CH2:31]1>>[F:12][C:31]1[CH:26]=[CH:27][C:28]([C:29]2[O:9][N:8]=[C:6]([C:5]3[CH:10]=[CH:11][CH:2]=[CH:3][CH:4]=3)[N:7]=2)=[CH:34][CH:30]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 5930004-Fluoro-n-hydroxybenzimidamideHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 4001499HCID 4001499, compoundYield 61%

Procedure

Benzyl-O-(4-fluorobenzamidoxime (116 mg, 449 mmol) was placed under nitrogen and THF (5.0 mL) was added. Then tetrabutylammonium fluoride (1.0 M, 450 μL) was added dropwise the solution was stirred at room temperature for 21 hours. The solid residue was purified by column chromatography over silica gel (EtOAc/Hex 1:8) and the product was crystallized from hot hexane to give clear crystals (66 mg, 61%). 1H NMR (300 MHz, CDCL3) δ(ppm): 7.23 (2H, t, J=8.3 Hz), 7.49-7.51 (3H, m), 8.16 (2H, dd, J=2.8, 6.9 Hz), 8.21 (2H, dd, J=5.4, 8.3 Hz). 13C NMR (75 MHz, CDCL3) δ(ppm): 116.7 (2CH, d, J=21.8 Hz), 127.0, 127.7 (CH), 129.1 (CH), 130.8 (CH), 131.1 (2CH, d, J=54.0 Hz), 163.9, 167.3, 169.18, 175.0. MS (FAB+): 241 (MH+). HRMS for C14H9FN2O (MH+): calculated: 241.0777; found 241.0759.

Workup

  1. customThe solid residue was purified by column chromatography over silica gel (EtOAc/Hex 1:8)
  2. customthe product was crystallized from hot hexane

Sources & evidence

ORD record
ord-115678e7830a4954a6e4e33df7337a32
Source dataset
uspto-grants-2015_06
Patent number
US09045442B2

Reaction notes

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