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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)-pyrrolidine

HRID 2214295
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Reaktionsgleichung

Reaktionsgleichung von HRID 2214295
[C:1]([Si:5]([CH3:50])([CH3:49])[O:6][C:7]1[CH:8]=[CH:9][C:10]([C:14]2[CH2:15][O:16][C:17]3[C:22]([C:23]=2[C:24]([OH:40])([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][N:35]4[CH2:39][CH2:38][CH2:37][CH2:36]4)=[CH:28][CH:27]=2)[CH3:25])=[CH:21][CH:20]=[C:19]([O:41][Si:42]([C:45]([CH3:48])([CH3:47])[CH3:46])([CH3:44])[CH3:43])[CH:18]=3)=[C:11](O)[CH:12]=1)([CH3:4])([CH3:3])[CH3:2].Cl>C1(C)C=CC=CC=1.O.C(OCC)(=O)C>[C:45]([Si:42]([CH3:44])([CH3:43])[O:41][C:19]1[CH:20]=[CH:21][C:22]2[C:23]3[C:24]([C:26]4[CH:27]=[CH:28][C:29]([O:32][CH2:33][CH2:34][N:35]5[CH2:36][CH2:37][CH2:38][CH2:39]5)=[CH:30][CH:31]=4)([CH3:25])[O:40][C:9]4[CH:8]=[C:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:2])[CH3:3])([CH3:49])[CH3:50])[CH:12]=[CH:11][C:10]=4[C:14]=3[CH2:15][O:16][C:17]=2[CH:18]=1)([CH3:46])([CH3:48])[CH3:47]
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Komponenten

6

Edukt 2

HCID 313Hydrochloric AcidHCID 219591555-(Tert-butyl-dimethyl-silyloxy)-2-(7-(tert-butyl-dimethyl-silyloxy)-4-{1-hydroxy-1-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-ethyl}-2H-chromen-3-yl)phenol

Produkt 1

HCID 219592841-(2-{4-[2,8-Bis-(tert-butyl-dimethyl-silyloxy)-5-methyl-5,11-dihydro-chromeno[4,3-c]chromen-5-yl]-phenoxy}-ethyl)-pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962Water
Lösungsmittel
HCID 1140TolueneLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

5-(Tert-butyl-dimethyl-silyloxy)-2-(7-(tert-butyl-dimethyl-silyloxy)-4-{1-hydroxy-1-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-ethyl}-2H-chromen-3-yl)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. The mixture was then diluted with water and ethyl acetate. The layers were separated and the 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 to yield the title compound as a light oil.

Aufarbeitung

  1. customThe layers were separated
  2. washthe organic 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-30f3c679f4304347b01725dbd569289d
Quelldatensatz
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07105679B2

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