Imidazole → HCID 68154456, Verbindung

HRID 73644Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 73644
[O:1]1[C@H:10]2[C:5](=[CH:6][CH2:7][CH2:8][C@H:9]2[CH2:11][OH:12])[CH2:4][CH2:3][CH2:2]1.CN(C=O)C.N1C=CN=C1.[C:23]([Si:27](Cl)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([CH3:26])([CH3:25])[CH3:24]>O>[C:23]([Si:27]([O:12][CH2:11][C@H:9]1[C@@H:10]2[C:5]([CH2:4][CH2:3][CH2:2][O:1]2)=[CH:6][CH2:7][CH2:8]1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)([CH3:26])([CH3:24])[CH3:25]

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 94078tert-ButyldiphenylchlorosilaneHCID 68154423HCID 68154423, Verbindung

Produkt 1

HCID 68154456HCID 68154456, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 360 mg (8S,8aR)-3,4,6,7,8,8a-hexahydro-2H-chromen-8-ylmethanol added 2.2 mL DMF, then 224 mg imidazole followed by 0.66 mL tert-butyl(chloro)diphenylsilane. The reaction was stirred overnight at RT, then added to water and extracted with diethyl ether. The crude extract was dried over Na2SO4, filtered, concentrated, then purified on silica gel to provide the title compound. 1H NMR (500 MHz, CDCl3) δ=1.05 (s, 9H), 1.37-1.46 (m, 1H), 1.54-1.58 (m, 1H), 1.63-1.73 (m, 2H), 1.86-2.09 (m, 3H), 2.16-2.24 (m, 1H), 2.25-2.31 (m, 1H), 3.53 (m, 1H), 3.60 (dd, J1=9.8 Hz, J2=7.7 Hz, 1H), 3.80 (d, J=5.1 Hz, 1H), 3.90 (dd, 10.0 Hz, J2=7.4 Hz, 1H), 3.94-3.98 (m, 1H), 4.49-5.52 (m, 1H), 7.35-7.42 (m, 6H), 7.67-7.72 (m, 4H) ppm.

Aufarbeitung

  1. extractionextracted with diethyl ether
  2. extractionThe crude extract
  3. dry with materialwas dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-c592335025fc4b5689d0023b3266e170
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829196B2

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