Tetrabutylammonium Fluoride → 1-(S)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(2-((tetrahydropyran-2-yl)oxy)-2-propyl)phenyl)-1-propanol

HRID 326934Notes

Reaction equation

HRID 326934 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:19][C:20]1[CH:29]=[C:28]2[C:23]([CH:24]=[CH:25][C:26]([CH:30]=[CH:31][C:32]3[CH:33]=[C:34]([C@@H:38]([O:57][Si](C)(C)C(C)(C)C)[CH2:39][CH2:40][C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=4[C:47]([O:50][CH:51]4[CH2:56][CH2:55][CH2:54][CH2:53][O:52]4)([CH3:49])[CH3:48])[CH:35]=[CH:36][CH:37]=3)=[N:27]2)=[CH:22][CH:21]=1>C1COCC1>[Cl:19][C:20]1[CH:29]=[C:28]2[C:23]([CH:24]=[CH:25][C:26]([CH:30]=[CH:31][C:32]3[CH:33]=[C:34]([C@@H:38]([OH:57])[CH2:39][CH2:40][C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=4[C:47]([O:50][CH:51]4[CH2:56][CH2:55][CH2:54][CH2:53][O:52]4)([CH3:49])[CH3:48])[CH:35]=[CH:36][CH:37]=3)=[N:27]2)=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 539396992-(2-(2-(3(S)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(dimethyl(2-methyl-2-propyl)silyloxy)propyl)phenyl)-2-propoxy)tetrahydropyran

Product 1

HCID 543944711-(S)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(2-((tetrahydropyran-2-yl)oxy)-2-propyl)phenyl)-1-propanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.0M Tetrabutylammonium fluoride in THF (85 mL) was added slowly to a solution of the product of Step 5 (33.31 g, 47 mmol) in 250 mL of anhydrous THF at 0° C. and the mixture was left in a refrigerator overnight and at r.t. for 4 h. 25% Aq. NH4OAc was then added and the product was extracted in EtOAc, dried over Na2SO4 and purified by flash chromatography on silica with EtOAc:toluene 10:90 and 15:85, to afford the title product. Yield of Steps 4-6: 81%.

Workup

  1. extractionthe product was extracted in EtOAc
  2. dry with materialdried over Na2SO4
  3. custompurified by flash chromatography on silica with EtOAc:toluene 10:90 and 15:85

Sources & evidence

ORD record
ord-bf08f899717f4cc39946c1ca620663d8
Source dataset
uspto-grants-1993_12
Patent number
US05270324

Reaction notes

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