Sodium hydride → HCID 21109460, Verbindung

HRID 1766124

Reaktionsgleichung

Reaktionsgleichung von HRID 1766124
[H-].[Na+].[Cl-].[CH3:4][O:5][C:6]1[CH:31]=[CH:30][C:9]([CH2:10][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:8][C:7]=1[CH3:32].[O:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]1[O:39][CH2:40][C:41]1[N:42]=[C:43]([C:48]2[CH:53]=[CH:52][C:51]([C:54]([F:57])([F:56])[F:55])=[CH:50][CH:49]=2)[S:44][C:45]=1[CH:46]=O>C(Cl)Cl.C(Cl)(Cl)(Cl)Cl>[CH3:4][O:5][C:6]1[CH:31]=[CH:30][C:9](/[CH:10]=[CH:46]/[C:45]2[S:44][C:43]([C:48]3[CH:53]=[CH:52][C:51]([C:54]([F:56])([F:57])[F:55])=[CH:50][CH:49]=3)=[N:42][C:41]=2[CH2:40][O:39][CH:34]2[CH2:35][CH2:36][CH2:37][CH2:38][O:33]2)=[CH:8][C:7]=1[CH3:32]

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 211094534-[(tetrahydro-2H-pyran-2-yloxy)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbaldehydeHCID 461800353-Methyl-4-methoxybenzyl triphenylphosphonium chloride

Produkt 1

HCID 21109460HCID 21109460, VerbindungAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5943Carbon TetrachlorideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of NaH (60% dispersion in mineral oil, 242 mg, 6.32 mmoles, 1.4 eq) in dry CH2Cl2 (15 ml) was added (4-Methoxy-3-methylbenzyl)(triphenyl)phosphonium chloride (2.62 g, 6.32 mmoles, 1.4 eq). This was allowed to stir at room temperature for 1.5 hours followed by the dropwise addition of 4-[(tetrahydro-2H-pyran-2-yloxy)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbaldehyde (1.68 g, 4.51 mmoles, 1 eq) in anhydrous carbon tetrachloride (25 ml). The resulting reaction mixture was refluxed overnight at which point (after cooling to room temperature) the reaction was washed with 1N NaOH, H2O, brine, dried over Na2SO4 and concentrated in vacuo to yield a >100% yield of a light green oil. The crude material was used without purification.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed overnight at which point (after cooling to room temperature) the reaction
  3. washwas washed with 1N NaOH, H2O, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-10452da0fe5a4d5c9bdcb7c2c92bd93d
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07229998B2

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