Water → 4-Isopropyl-2-[4-(trifluoromethyl)phenyl]thiazole-5-methanol

HRID 1173043

Reaktionsgleichung

Reaktionsgleichung von HRID 1173043
[CH3:1][CH:2]([C:4]1[N:5]=[C:6]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[S:7][C:8]=1[C:9](OCC)=[O:10])[CH3:3].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH3:3][CH:2]([C:4]1[N:5]=[C:6]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:16][CH:15]=2)[S:7][C:8]=1[CH2:9][OH:10])[CH3:1]

Komponenten

6

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 587658244-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester

Produkt 1

HCID 587657624-Isopropyl-2-[4-(trifluoromethyl)phenyl]thiazole-5-methanolAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Ethyl 4-(1-methylethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylate (XI-5a) (2.68 g, 7.80 mmol) was dissolved in THF (8 mL) and cooled to 0° C. under nitrogen. Lithium aluminum hydride (1.0M solution in THF, 8.00 mL, 8.00 mmol) was added and the mixture was stirred at 0° C. for 60 min. Water (0.3 mL) was added, followed by 15% aqueous sodium hydroxide (0.3 mL), then water (0.9 mL). The resulting mixture was filtered and the filtrate was concentrated to provide the title compound (2.13 g, 91%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 8.03 (d, J=8.3 Hz, 2H), 7.65 (d, J=8.3 Hz, 2H), 4.86 (d, J=5.2 Hz, 2H), 3.14 (qu, J=6.8 Hz, 1H), 1.33 (d, J=6.8 Hz, 6H).

Aufarbeitung

  1. filtrationThe resulting mixture was filtered
  2. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-3e5a982c3e954366ad0294e38906baf8
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834013B2

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