Tetrabutylammonium Fluoride → HCID 58366210, compound

HRID 877393Notes

Reaction equation

HRID 877393 reaction equation
[Si]([O:8][CH:9]([C:22]1[N:23]=[N:24][N:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)[N:26]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(C(C)(C)C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOC(C)=O>[C:16]1([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH:9]([C:22]2[N:23]=[N:24][N:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)[N:26]=2)[OH:8])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58366252HCID 58366252, compound

Product 1

HCID 58366210HCID 58366210, compoundYield 88.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(5-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)-2H-tetrazol-2-yl)-pyridine (4.4 mg, 0.009 mmol) was dissolved in THF (122 μL), treated with Bu4NF (1 M in THF, 0.013 mL, 0.013 mmol) and stirred at room temperature for 2 h under Ar. The reaction mixture was diluted with EtOAc, washed with saturated aqueous NaCl and dried over Na2SO4. Evaporation in vacuo yielded the crude alcohol that was purified by flash chromatography (SiO2, 0.5×4 cm, 20-50% EtOAc-hexanes) to afford 7-phenyl-1-(2-(pyridin-2-yl)-2H-tetrazol-5-yl)-heptan-1-ol (2.7 mg, 79%) as a white solid: 1H NMR (CDCl3, 600 MHz) δ 8.69 (dd, 1H, J=1.1, 4.7 Hz), 8.18 (d, 1H, J=8.1 Hz), 8.00 (m, 1H), 7.50 (ddd, 1H, J=0.7, 4.8, 7.4 Hz), 7.26 (m, 2H), 7.16 (m, 3H), 5.16 (m, 1H), 2.59 (t, 2H, J=7.7 Hz), 2.48 (d, 1H(—OH), J=6.1 Hz), 2.07 (m, 2H), 1.61 (m, 2H), 1.52 (m, 2H), 1.40 (m, 4H); 13C NMR (CDCl3, 150 MHz) δ 169.5, 149.6, 148.8, 142.9, 139.6, 128.5, 128.4, 125.7, 125.3, 115.3, 67.0, 36.7, 36.1, 31.5, 29.3 (2C), 25.2; HRMS-ESI-TOF m/z 338.1966 ([M+H]+, C19H23N5O requires 338.1975).

Workup

  1. washwashed with saturated aqueous NaCl
  2. dry with materialdried over Na2SO4
  3. customEvaporation in vacuo
  4. customyielded the crude alcohol that
  5. customwas purified by flash chromatography (SiO2, 0.5×4 cm, 20-50% EtOAc-hexanes)

Sources & evidence

ORD record
ord-b8eaa939622a4e5fad1128b09f4672d5
Source dataset
uspto-grants-2015_03
Patent number
US08987312B2

Reaction notes

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