Lithium tri-tert-butoxyaluminohydride → HCID 56605060, Verbindung
Reaktionsgleichung
[C:1]([O:9][CH2:10][C@@H:11]1[C@@H:15]([O:16][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@:14]([F:26])([CH3:25])[C:13](=[O:27])[O:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C(O[Al](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+]>>[C:1]([O:9][CH2:10][C@@H:11]1[C@@H:15]([O:16][C:17](=[O:24])[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@:14]([F:26])([CH3:25])[CH:13]([OH:27])[O:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Komponenten
3
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a stirred solution of ((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate (about 60 g, 161 mmol) in tetrahydrafuran (about 300 ml) cooled to about −10° C., then lithium tri tertiary butoxy aluminum hydride (about 241.9 ml, 241 mmol) was added and stirred at about 0° C. for 1 hour. Completion of the reaction was monitored by thin layer chromatography, quenched with saturated ammonium chloride solution. Tetrahydrafuran was removed under reduced pressure and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with water, brine and dried over sodium sulphate. The organic layer was removed under reduced pressure and the residue was purified by silica gel column chromatography using 16% ethyl acetate: hexane as eluent furnished title compound (about 60 g) as a colorless liquid. Yield: 99.46%; 1H NMR (300 MHz, CDCl3): δ 8.11-8.00 (m, 4H), 7.61-7.37 (m, 6H), 5.65 (dd, 1H, J=23.4 Hz, 7.8 Hz, 7.5 Hz), 5.34 (dd, 1H, J=9.6 Hz, 2.7 Hz), 4.69-4.66 (m, 1H), 4.57-4.53 (m, 2H), 3.40 (brs, 1H, —OH), 1.60-1.56 (m, 3H, J=22.5); Mass: [M+Na]+: 397 (100%); IR cm−: 3439, 3070, 2940, 2868, 1733, 1729, 1453, 1274, 1115, 710.