Sodium Iodide → (1R)-1-(4,5-diphenyloxazol-2-yl)methyloxy-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene

HRID 1741364Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1741364
[OH:1][C@H:2]1[C:11]2[C:6](=[C:7]([O:12][Si:13]([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1.C([Li])CCC.[C:35]1([C:41]2[N:42]=[C:43]([CH2:52]Br)[O:44][C:45]=2[C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[Na+].[I-]>C1COCC1.O.C(OCC)(=O)C>[C:35]1([C:41]2[N:42]=[C:43]([CH2:52][O:1][C@H:2]3[C:11]4[C:6](=[C:7]([O:12][Si:13]([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[C:14]5[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=5)[CH:8]=[CH:9][CH:10]=4)[CH2:5][CH2:4][CH2:3]3)[O:44][C:45]=2[C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Komponenten

8

Edukt 4

HCID 5238Sodium IodideHCID 5685992-Bromomethyl-4,5-diphenyl-oxazoleHCID 54062035(1R)-1-hydroxy-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthaleneHCID 178418339Butyllithium

Produkt 1

HCID 54555965(1R)-1-(4,5-diphenyloxazol-2-yl)methyloxy-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthaleneAusbeute 69,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (1R)-1-hydroxy-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene (1.5 g) in THF (20 ml) were added n-butyllithium (2.8 ml, 1.5M solution in hexane), (4,5-diphenyloxazol-2-yl)methyl bromide (1.8 g) and NaI (1.2 g) at -78° C. under N2. The solution was warmed to the room temperature and stirred for 6 hours. The mixture was poured into a mixture of ethyl acetate and water. The organic layer was washed with 1N-HCl solution, sat. NaHCO3 and brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford (1R)-1-(4,5-diphenyloxazol-2-yl)methyloxy-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene (1.65 g). MS (m/z): 636 (M+ +1) IR (Neat): 3400 cm-1NMR (CDCl3, δ): 1.09 (9H, s), 1.6-2.2 (4H, m), 2.6-3.2 (2H, m), 4.65 (1H, m), 4.75 (1H, d, J=13.2 Hz), 4.84 (1H, d, J=13.2 Hz), 6.31 (1H, d, J=8 Hz), 6.75 (1H, t, J=8 Hz), 6.98 (1H, d, J=8 Hz), 7.2-7.8 (10H, m)

Aufarbeitung

  1. washThe organic layer was washed with 1N-HCl solution, sat. NaHCO3 and brine
  2. dry with materialdried over MgSO4
  3. customevaporated in vacuo
  4. customThe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-a2c7674cf17141e0922f21bdf2239859
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05972965

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