Aluminium lithium hydride → (S)-(5-methyl-2-(pent-4-en-2-yloxy)phenyl)methanol
Reaktionsgleichung
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][C@H:13]([CH2:15][CH:16]=[CH2:17])[CH3:14])=[C:6]([CH:11]=1)[C:7](OC)=[O:8].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][C@H:13]([CH2:15][CH:16]=[CH2:17])[CH3:14])=[C:6]([CH2:7][OH:8])[CH:11]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of (S)-methyl 5-methyl-2-(pent-4-en-2-yloxy)benzoate (1.2664 g, 5.41 mmol) in THF (15 ml) cooled to 0° C. was added dropwise lithium aluminum hydride (3.25 ml, 6.49 mmol). The mixture was stirred at rt for 2 h then cooled to 0° C. and quenched by the dropwise addition of brine. The mixture was partitioned between EtOAc and water. The organic phase was washed with brine, dried (Na2SO4), filtered and concentrated to give (S)-(5-methyl-2-(pent-4-en-2-yloxy)phenyl)methanol (0.8702 g, 4.22 mmol, 78% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.14-7.01 (m, 2H), 6.80 (d, J=8.1 Hz, 1H), 6.01-5.74 (m, 1H), 5.24-5.04 (m, 2H), 4.76-4.64 (m, 1H), 4.64-4.56 (m, 1H), 4.51 (sxt, J=6.0 Hz, 1H), 2.63-2.48 (m, 2H), 2.48-2.41 (m, 1H), 2.30 (s, 3H), 1.37 (d, J=6.1 Hz, 3H).