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Triethylamine → 2-(4,5-Diphenyloxazol-2-yl)-3-(3-t-butyldiphenylsilyloxybenzyl)tetrahydrothiophene

HRID 1741357
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Reaktionsgleichung

Reaktionsgleichung von HRID 1741357
[C:1]1([C:7]2[N:8]=[C:9]([CH:18](O)[CH:19]([CH2:45][CH2:46]O)[CH2:20][C:21]3[CH:22]=[C:23]([O:27][Si:28]([C:41]([CH3:44])([CH3:43])[CH3:42])([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH:24]=[CH:25][CH:26]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[S:50](Cl)(=O)=O.C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[C:1]1([C:7]2[N:8]=[C:9]([CH:18]3[CH:19]([CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([O:27][Si:28]([C:41]([CH3:44])([CH3:43])[CH3:42])([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)[C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[CH:22]=4)[CH2:45][CH2:46][S:50]3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
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Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 183674053-[3-(4,5-Diphenyloxazol-2-yl)-3-hydroxy-2-(2-hydroxyethyl)propyl]-1-(t-butyldiphenylsilyloxy)benzene

Produkt 1

HCID 183674322-(4,5-Diphenyloxazol-2-yl)-3-(3-t-butyldiphenylsilyloxybenzyl)tetrahydrothiophene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028
Tetrahydrofuran
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 3-[3-(4,5-diphenyloxazol-2-yl)-3-hydroxy-2-(2-hydroxyethyl)propyl]-1-(t-butyldiphenylsilyloxy)benzene (3.0 g) and methanesulfonyl chloride (1.1 ml) and triethylamine (2.6 ml) in THF (50 ml) was stirred at room temperature for 1 hour. The solution was diluted with ethyl acetate and washed with sat. NaHCO3 and brine, dried over MgSO4, and evaporated. The residue was dissolved in DMF (40 ml) and to the solution was added Na2S (600 mg). After being stirred for 30 minutes at 80° C., the mixture was partitioned between ethyl acetate and water. The organic layer was washed with water, sat. NaHCO3, and brine. The dried solvent was evaporated in vacuo and the residue was purified by chromatography on silica gel to afford 2-(4,5-diphenyloxazol-2-yl)-3-(3-t-butyldiphenylsilyloxybenzyl)tetrahydrothiophene (3.2 g). MS (m/z): 652 (M+ +1) IR (Neat): 1600, 1580 cm-1NMR (CDCl3, δ): 1.08 (9H, s), 2.0-2.5 (4H, m), 2.6-3.2 (3H, m), 4.10 (2/3H, d, J=7 Hz), 4.20 (1/3H, d, J=7 Hz), 6.4-6.8 (3H, m), 6.9-7.1 (1H, m), 7.2-7.8 (20H, m)

Aufarbeitung

  1. washwashed with sat. NaHCO3 and brine
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. dissolutionThe residue was dissolved in DMF (40 ml) and to the solution
  5. additionwas added Na2S (600 mg)
  6. stirringAfter being stirred for 30 minutes at 80° C.
  7. customthe mixture was partitioned between ethyl acetate and water
  8. washThe organic layer was washed with water, sat. NaHCO3, and brine
  9. customThe dried solvent was evaporated in vacuo
  10. customthe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-ad90cf60c9d44cc0a36785929c2ffe90
Quelldatensatz
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05972965

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