Tetrabutylammonium Fluoride → HCID 19756350, compound

HRID 1587827Notes

Reaction equation

HRID 1587827 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:36][CH2:37][CH2:38][O:39][C:40]1[N:41]=[C:42]2[C:47](=[CH:48][CH:49]=1)[N:46]=[C:45]([CH2:50][CH3:51])[CH:44]=[C:43]2[O:52][CH2:53][C:54]1[CH:59]=[CH:58][C:57]([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=2[C:66]2[N:67]=[N:68][N:69]([C:71]([C:84]3[CH:89]=[CH:88][CH:87]=[CH:86][CH:85]=3)([C:78]3[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=3)[C:72]3[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=3)[N:70]=2)=[CH:56][CH:55]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>O1CCCC1.C(OCC)(=O)C>[CH2:50]([C:45]1[CH:44]=[C:43]([O:52][CH2:53][C:54]2[CH:55]=[CH:56][C:57]([C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=3[C:66]3[N:67]=[N:68][N:69]([C:71]([C:84]4[CH:85]=[CH:86][CH:87]=[CH:88][CH:89]=4)([C:78]4[CH:79]=[CH:80][CH:81]=[CH:82][CH:83]=4)[C:72]4[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=4)[N:70]=3)=[CH:58][CH:59]=2)[C:42]2[C:47](=[CH:48][CH:49]=[C:40]([O:39][CH2:38][CH2:37][OH:36])[N:41]=2)[N:46]=1)[CH3:51]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 53976296HCID 53976296, compound

Product 1

HCID 19756350HCID 19756350, compoundYield 89.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A 1M solution of tetrabutylammonium fluoride in tetrahydrofuran (THF) (67.8 ml) was added to a solution of compound E (32.1 g) in dry THF (400 ml), and the solution was left to stand for 1 hour. The solution was then diluted with ethyl acetate (400 ml), washed with water (400 ml) and dried (MgSO4). Volatile material was removed by evaporation, and the residue triturated with ether to give 2-ethyl-6-(2-hydroxyethoxy)-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]-1,5-naphthyridine (A) (21.6 g), as a white solid, m.p. 170°-173° C.; NMR (d6 -DMSO): 1.3(t,3H), 2.85(q,2H), 3.75(q,2H), 4.45(t,2H), 4.85(t,1H), 5.35(s,2H), 6.8-6.9(m,7H), 7.1-7.7 (complex m,17H), 7.8(dd,1H), 8.15(d,1H).

Workup

  1. waitthe solution was left
  2. washwashed with water (400 ml)
  3. dry with materialdried (MgSO4)
  4. customVolatile material was removed by evaporation
  5. customthe residue triturated with ether

Sources & evidence

ORD record
ord-1998c13414f04aca82fe5466a6851935
Source dataset
uspto-grants-1993_06
Patent number
US05219863

Reaction notes

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