Ammonium Chloride → 3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-[5-(4-ethylphenyl)methyl-2-(2-trityloxyethyl)thiophen-3-yl]-tetrahydropyran-2-ol

HRID 499731Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 499731
Br[C:2]1[CH:6]=[C:5]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH3:15])=[CH:10][CH:9]=2)[S:4][C:3]=1[CH2:16][CH2:17][O:18][C:19]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([Li])CCC.[CH2:43]([O:50][CH:51]1[CH:56]([O:57][CH2:58][C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[CH:55]([O:65][CH2:66][C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=2)[CH:54]([CH2:73][O:74][CH2:75][C:76]2[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=2)[O:53][C:52]1=[O:82])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.[Cl-].[NH4+]>C1COCC1.CCCCCC>[CH2:43]([O:50][CH:51]1[CH:56]([O:57][CH2:58][C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[CH:55]([O:65][CH2:66][C:67]2[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=2)[CH:54]([CH2:73][O:74][CH2:75][C:76]2[CH:77]=[CH:78][CH:79]=[CH:80][CH:81]=2)[O:53][C:52]1([C:2]1[CH:6]=[C:5]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH3:15])=[CH:10][CH:9]=2)[S:4][C:3]=1[CH2:16][CH2:17][O:18][C:19]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[OH:82])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 45855083,4,5-Tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-oneHCID 684604163-Bromo-5-((4-ethylphenyl)methyl)-2-(2-trityloxyethyl)thiopheneHCID 178418339Butyllithium

Produkt 1

HCID 866266373,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-[5-(4-ethylphenyl)methyl-2-(2-trityloxyethyl)thiophen-3-yl]-tetrahydropyran-2-olAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

Under a nitrogen stream, to a solution of 3-bromo-5-((4-ethylphenyl)methyl)-2-(2-trityloxyethyl)thiophene (1.45 g, 2.55 mmol) in anhydrous THF (40 ml), a hexane solution of n-butyllithium (1.6 M, 1.76 ml, 2.81 mmol) was added dropwise at −78° C. and the mixture was stirred for 15 minutes. To this solution was added a solution of 3,4,5-trisbenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-one (1.50 g, 2.81 mmol) in anhydrous THF (10 ml) dropwise at −78° C. and the resulting solution was stirred at the same temperature for 10 minutes. After addition of saturated aqueous ammonium chloride, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and then evaporated under reduced pressure to remove the solvent. The resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:20)) to give the titled compound (1.70 g, 65%).

Aufarbeitung

  1. stirringthe resulting solution was stirred at the same temperature for 10 minutes
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated under reduced pressure
  6. customto remove the solvent
  7. customThe resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:20))

Quellen und Nachweise

ORD-Eintrag
ord-be7255b86c9e47069d6c76538c2b9a07
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767651B2

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