Tetrabutylammonium Fluoride → HCID 58514462, compound

HRID 341294Notes

Reaction equation

HRID 341294 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1(S([N:28]2[C:36]3[C:31](=[CH:32][C:33]([C:37]4[CH:42]=[CH:41][C:40]([CH2:43][N:44]5[CH2:49][CH2:48][O:47][CH2:46][CH2:45]5)=[CH:39][CH:38]=4)=[CH:34][CH:35]=3)[C:30]3[CH:50]=[C:51]([Cl:54])[CH:52]=[N:53][C:29]2=3)(=O)=O)C=CC=CC=1>C1COCC1>[Cl:54][C:51]1[CH:52]=[N:53][C:29]2[NH:28][C:36]3[C:31]([C:30]=2[CH:50]=1)=[CH:32][C:33]([C:37]1[CH:38]=[CH:39][C:40]([CH2:43][N:44]2[CH2:45][CH2:46][O:47][CH2:48][CH2:49]2)=[CH:41][CH:42]=1)=[CH:34][CH:35]=3

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58514558HCID 58514558, compound

Product 1

HCID 58514462HCID 58514462, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

At Room Temperature and Under Inert Atmosphere, 1.0 M TBAF in THF (1.75 mL, 5 equiv.) was added a solution of 30 (181 mg, 0.35 mmol) in anhydrous THF (16 mL). The solution was refluxed for 4 h. The resulting mixture was then cautiously quenched at 0° C. with H2O. The mixture was extracted with EtOAc (3×20 mL). The resulting organic layers were dried over MgSO4, filtered, and solvents were removed under reduced pressure. The crude product was purified by flash chromatography (eluent: CH2Cl2/EtOAc 7:3 to EtOAc) to afford R313 in 61% yield as a yellow solid; 1H-NMR (300 MHz, DMSO-d6): δ 12.05 (bs, 1H), 8.75 (d, 1H, J=2.4 Hz), 8.55 (d, 1H, J=1.7 Hz), 8.43 (d, 1H, J=2.4 Hz), 7.81 (dd, 1H, J=1.7, 8.7 Hz), 7.70 (d, 2H, J=8.1 Hz), 7.58 (d, 1H, J=8.7 Hz), 7.41 (d, 2H, J=8.1 Hz), 3.59 (t, 4H, J=4.4 Hz), 3.51 (s, 2H), 2.39 (t, 4H, J=4.4 Hz); 13C-NMR (75 MHz, DMSO-d6): δ 150.6 (C), 144.2 (C), 139.5 (C), 139.2 (C), 136.3 (C), 132.3 (C), 129.6 (2 CH), 128.3 (C), 126.5 (2 CH), 126.4 (CH), 121.8 (C), 120.2 (C), 119.8 (CH), 116.7 (C), 111.9 (CH), 66.2 (2 CH2), 62.1 (CH2), 53.2 (2 CH2); MS (ESI) m/z 378 [M+H+]

Workup

  1. temperatureThe solution was refluxed for 4 h
  2. customThe resulting mixture was then cautiously quenched at 0° C. with H2O
  3. extractionThe mixture was extracted with EtOAc (3×20 mL)
  4. dry with materialThe resulting organic layers were dried over MgSO4
  5. filtrationfiltered
  6. customsolvents were removed under reduced pressure
  7. customThe crude product was purified by flash chromatography (eluent: CH2Cl2/EtOAc 7:3 to EtOAc)
  8. customto afford R313 in 61% yield as a yellow solid

Sources & evidence

ORD record
ord-75ad1592abe54cb0a0017e1393a08c9a
Source dataset
uspto-grants-2014_11
Patent number
US08895744B2

Reaction notes

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