Sodium hydride → 4-[2-(4-Bromophenyl)vinyl]-4-(t-butyldimethylsilanyloxymethyl)-2-methyl-4,5-dihydrooxazole

HRID 1375922Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1375922
[Br-].[Br:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:5][CH:4]=1.[H-].[Na+].[Si:31]([O:38][CH2:39][C:40]1([CH:46]=O)[CH2:44][O:43][C:42]([CH3:45])=[N:41]1)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]>C1COCC1>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([CH:7]=[CH:46][C:40]2([CH2:39][O:38][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:32])[CH3:33])[CH2:44][O:43][C:42]([CH3:45])=[N:41]2)=[CH:27][CH:28]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 2724858[(4-Bromophenyl)methyl]triphenylphosphanium bromideHCID 58787875HCID 58787875, Verbindung

Produkt 1

HCID 694272274-[2-(4-Bromophenyl)vinyl]-4-(t-butyldimethylsilanyloxymethyl)-2-methyl-4,5-dihydrooxazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of (4-bromobenzyl)triphenyl-phosphonium bromide (6 mmol) in dry THF (25 mL) is added NaH (6 mmol) in portions. After stirring at room temperature for 30 min, a solution of 4-(t-butyidimethylsilanyloxymethyl)-2-methyl-4,5-dihydrooxazole-4-carbaldehyde (prepared according to Scheme 3 using well-known chemistry in the art) (5 mmol) in THF (10 mL) is added in one portion. The mixture is stirred at room temperature for 12 h. After concentration, the residue is treated with EtOAc/hexane (1/5) (100 mL) and the solid is filtrated. The filtrate is washed with brine and dried over Na2SO4. After concentration, the crude product is purified by column chromatography by EtOAc/hexane (1/5) to give the desired product as a colorless oil. MS: (ES+): 410.1 (M+1)+.

Aufarbeitung

  1. additionis added in one portion
  2. stirringThe mixture is stirred at room temperature for 12 h
  3. concentrationAfter concentration
  4. additionthe residue is treated with EtOAc/hexane (1/5) (100 mL)
  5. filtrationthe solid is filtrated
  6. washThe filtrate is washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationAfter concentration
  9. customthe crude product is purified by column chromatography by EtOAc/hexane (1/5)

Quellen und Nachweise

ORD-Eintrag
ord-c01446a4631e4b00ba1f819272a51edf
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07169817B2

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