Aluminium lithium hydride → 4-(2,3-Dihydrobenzofuran-7-yl)-4-methyl-2-(trifluoromethyl)pentane-1,2-diol
Reaktionsgleichung
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10](=O)[C:11]([OH:29])([C:25]([F:28])([F:27])[F:26])[CH2:12][C:13]([C:16]1[C:24]2[O:23][CH2:22][CH2:21][C:20]=2[CH:19]=[CH:18][CH:17]=1)([CH3:15])[CH3:14])C>C1COCC1>[O:23]1[C:24]2[C:16]([C:13]([CH3:15])([CH3:14])[CH2:12][C:11]([C:25]([F:26])([F:27])[F:28])([OH:29])[CH2:10][OH:9])=[CH:17][CH:18]=[CH:19][C:20]=2[CH2:21][CH2:22]1Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
A suspension of LiAlH4 (4.52 g, 119 mmol) in 230 mL of THF was treated with a solution of 4-(2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethylpentanoic acid ethyl ester (27.5 g, 79.4 mmol) in 40 mL of THF at 0° C. over 30 minutes. After stirring overnight, the reaction was cooled to 0° C., quenched with 3 mL of water, and treated with 3 mL of 4 M NaOH solution. After 10 minutes, the mixture was treated with additional 18 mL portion of water and the resulting mixture was warmed to room temperature for 4 hours. The mixture was filtered and the filter cake was washed with five 100 mL portions of diethyl ether. The filtrate was concentrated in vacuo to give 24.0 g of 4-(2,3-dihydrobenzofuran-7-yl)-4-methyl-2-trifluoromethylpentane-1,2-diol as an oil (99%).
Aufarbeitung
- customquenched with 3 mL of water
- additiontreated with 3 mL of 4 M NaOH solution
- waitAfter 10 minutes
- additionthe mixture was treated with additional 18 mL portion of water
- temperaturethe resulting mixture was warmed to room temperature for 4 hours
- filtrationThe mixture was filtered
- washthe filter cake was washed with five 100 mL portions of diethyl ether
- concentrationThe filtrate was concentrated in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-29f2bcb0d3b74666bfa83543a49f961e
- Quelldatensatz
- uspto-grants-2012_09
- Patentnummer
- US08268859B2
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