Diethyl Ether → 2-(1-benzyl-2-hydroxymethyl-1H-indol-5-yl)-1,1,1,3,3,3-hexafluoro-propan-2-ol

HRID 1724028Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1724028
C(N1C2C(=CC=CC=2)C([C:17]([OH:26])([C:22]([F:25])([F:24])[F:23])[C:18]([F:21])([F:20])[F:19])=C1CO[Si](C(C)C)(C(C)C)C(C)C)C1C=CC=CC=1.[F-].C([N+:44]([CH2:53][CH2:54][CH2:55][CH3:56])([CH2:49][CH2:50][CH2:51][CH3:52])[CH2:45][CH2:46][CH2:47][CH3:48])CCC.[NH4+].[Cl-].C[CH2:60][O:61]CC.[CH2:64]1[CH2:68]OC[CH2:65]1>>[CH2:53]([N:44]1[C:45]2[C:51](=[CH:52][C:48]([C:17]([OH:26])([C:22]([F:23])([F:24])[F:25])[C:18]([F:20])([F:19])[F:21])=[CH:47][CH:46]=2)[CH:50]=[C:49]1[CH2:60][OH:61])[C:54]1[CH:55]=[CH:56][CH:68]=[CH:64][CH:65]=1

Komponenten

6

Edukt 5

HCID 3283Diethyl EtherHCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 867608102-(1-benzyl-2-triisopropylsilanyloxymethyl-1H-indol--yl)-1,1,1,3,3,3-hexafluoro-propan-2-ol

Produkt 1

HCID 115604542-(1-benzyl-2-hydroxymethyl-1H-indol-5-yl)-1,1,1,3,3,3-hexafluoro-propan-2-ol

Versuchsvorschrift

To a solution of 0.93 g (1.66 mmol) of 2-(1-benzyl-2-triisopropylsilanyloxymethyl-1H-indol--yl)-1,1,1,3,3,3-hexafluoro-propan-2-ol in 10 mL of THF were added 1.66 mL (1.66 mmol) of a 1 M solution of tetrabutyl ammonium fluoride in THF. The mixture was stirred at RT for 1 h and poured into a mixture of a saturated aqueous solution of NH4Cl and Et2O. The phases were separated and the aqueous one was extracted with Et2O. The combined organic phases were dried over Na2SO4 and evaporated to yield 1.0 g (quantitative) of 2-(1-benzyl-2-hydroxymethyl-1H-indol-5-yl)-1,1,1,3,3,3-hexafluoro-propan-2-ol, light yellow semisolid, MS: 402 (M−H)−.

Aufarbeitung

  1. customThe phases were separated
  2. extractionthe aqueous one was extracted with Et2O
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-5981af55b50b4093886a2e71a3d70f1a
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07485652B2

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