HCID 178471800, Verbindung → HCID 178471796, Verbindung
Reaktionsgleichung
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12](O)=[O:13])[CH2:8][CH2:7]1)[CH3:2]>C1COCC1>[OH:13][CH2:12][C@H:9]1[CH2:10][CH2:11][C@H:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:15])[CH2:7][CH2:8]1Komponenten
3
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of trans-4-(2-ethoxy-2-oxoethyl)cyclohexanecarboxylic acid (385.6 mg, 1.80 mmol) in THF (20 mL) was added BH3 (2.7 mL of a 1M solution in THF, 2.70 mmol). After 2 hours, the reaction was quenched by careful addition of H2O (10 mL). The mixture was extracted with EtOAc (80 mL) and the organic layer was washed with water and brine (20 mL each). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by flash chromatography on silica gel (5 to 60% EtOAc/hexanes) afforded ethyl [trans-4-(hydroxymethyl)cyclohexyl]acetate. Rf=0.26 (40% EtOAc/hexanes). 1H NMR (CDCl3, 600 MHz) δ 4.12 (q, J=7.1 Hz, 2H), 3.45 (d, J=6.5 Hz, 2H), 2.19 (d, J=7.0 Hz, 2H), 1.72-1.82 (m, 5H), 1.45 (m, 1H), 1.25 (t, J=7.1 Hz, 3H), 0.96-1.05 (m, 4H).