Hydrochloric Acid → 1-(2-{4-[2,8-Bis-(tert-butyl-dimethyl-silyloxy)-5-methyl-5,11-dihydro-chromeno[4,3-c]chromen-5-yl]-phenoxy}-ethyl)-azepane

HRID 2214298Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2214298
[N:1]1([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])=[CH:27][CH:28]=4)[O:23][CH2:22][C:21]=3[C:38]3[CH:43]=[CH:42][C:41]([O:44][Si:45]([C:48]([CH3:51])([CH3:50])[CH3:49])([CH3:47])[CH3:46])=[CH:40][C:39]=3O)([OH:19])[CH3:18])=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>C1(C)C=CC=CC=1.O.C(OCC)(=O)C>[C:34]([Si:31]([CH3:32])([CH3:33])[O:30][C:26]1[CH:27]=[CH:28][C:29]2[C:20]3[C:17]([C:14]4[CH:15]=[CH:16][C:11]([O:10][CH2:9][CH2:8][N:1]5[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]5)=[CH:12][CH:13]=4)([CH3:18])[O:19][C:39]4[CH:40]=[C:41]([O:44][Si:45]([C:48]([CH3:50])([CH3:51])[CH3:49])([CH3:47])[CH3:46])[CH:42]=[CH:43][C:38]=4[C:21]=3[CH2:22][O:23][C:24]=2[CH:25]=1)([CH3:35])([CH3:36])[CH3:37]

Komponenten

6

Edukt 2

HCID 313Hydrochloric AcidHCID 693277712-[4-{-1-[4-(2-azepan-1-yl-ethoxy)-phenyl]-1-hydroxy-ethyl}-7-(tert-butyl-dimehyl-silyloxy)-2H-chromen-3-yl]-5-(tert-butyl-dimethyl-silyloxy)-phenol

Produkt 1

HCID 219592481-(2-{4-[2,8-Bis-(tert-butyl-dimethyl-silyloxy)-5-methyl-5,11-dihydro-chromeno[4,3-c]chromen-5-yl]-phenoxy}-ethyl)-azepane

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-[4-{1-[4-(2-azepan-1-yl-ethoxy)-phenyl]-1-hydroxy-ethyl}-7-(tert-butyl-dimehyl-silyloxy)-2H-chromen-3-yl]-5-(tert-butyl-dimethyl-silyloxy)-phenol, prepared as in STEP A above, was dissolved in toluene (8 mL) and treated with diluted HCl (0.4 mL of concentrated HCl:H2O=1:2 v/v). The reaction mixture was vigorously stirred at room temperature for 1.5 h, then diluted with water and ethyl acetate. The resulting layers were separated and organic layer washed successively with saturated NaHCO3, brine and dried over MgSO4. The desiccant was filtered off, and the filtrate concentrated. Flash chromatography with ethyl acetate:hexane:CH3OH (containing 1% NH4OH)=49:49:2 as the eluent yielded the title compound as a light yellow oil.

Aufarbeitung

  1. customThe resulting layers were separated
  2. washorganic layer washed successively with saturated NaHCO3, brine
  3. dry with materialdried over MgSO4
  4. filtrationThe desiccant was filtered off
  5. concentrationthe filtrate concentrated

Quellen und Nachweise

ORD-Eintrag
ord-82f97b7d123945038df2a330bf61f707
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07105679B2

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