Tetrabutylammonium Fluoride → 5,7-diethyl-1-(4-hydroxy-3-propylbenzyl)-1,6-naphthyridin-2(1H)-one

HRID 1492308Notes

Reaction equation

HRID 1492308 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][C:27]1[CH:48]=[CH:47][C:30]([CH2:31][N:32]2[C:41]3[C:36](=[C:37]([CH2:44][CH3:45])[N:38]=[C:39]([CH2:42][CH3:43])[CH:40]=3)[CH:35]=[CH:34][C:33]2=[O:46])=[CH:29][C:28]=1[CH2:49][CH2:50][CH3:51])(C(C)(C)C)(C)C>O1CCCC1>[CH2:44]([C:37]1[N:38]=[C:39]([CH2:42][CH3:43])[CH:40]=[C:41]2[C:36]=1[CH:35]=[CH:34][C:33](=[O:46])[N:32]2[CH2:31][C:30]1[CH:47]=[CH:48][C:27]([OH:26])=[C:28]([CH2:49][CH2:50][CH3:51])[CH:29]=1)[CH3:45]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 189523981-[4-(t-butyldimethylsilyloxy)-3-propylbenzyl]-5,7-diethyl-1,6-naphthyridin-2(1H)-one

Product 1

HCID 189523935,7-diethyl-1-(4-hydroxy-3-propylbenzyl)-1,6-naphthyridin-2(1H)-oneYield 79.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.0M Tetrabutylammonium fluoride in tetrahydrofuran (2 ml) was added to a stirred solution of compound E (0.9 g) in tetrahydrofuran (8 ml) under an atmosphere of argon. The solution was left to stand for 2 hours and then volatile material was removed by evaporation. The residue was purified by flash chromatography, eluting with ethyl acetate, to give 5,7-diethyl-1-(4-hydroxy-3-propylbenzyl)-1,6-naphthyridin-2(1H)-one (F) (0.54 g) as a foam; NMR: 0.9(t, 3H), 1.2(t, 3H), 1.3(t, 3H), 1.55-1.65(m, 2H), 2.55(t, 2H), 2.8(q, 2H), 3.1(q, 2H), 5.4(s, 2H), 5.5(br s, 1H), 6.65(d, 1H), 6.75(d, 1H), 6.9(d, 1H), 6.95(s, 1H), 7.05(s, 1H), 7.95(d, 1H).

Workup

  1. waitThe solution was left
  2. customvolatile material was removed by evaporation
  3. customThe residue was purified by flash chromatography
  4. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-5dbc48c07e4e4d509ce02a699880fb0b
Source dataset
uspto-grants-1994_12
Patent number
US05373015

Reaction notes

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