* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference：
[1] Journal of the American Chemical Society, 1968, vol. 90, p. 7001 - 7007
2
[ 6317-49-3 ]
[ 22515-16-8 ]
Reference：
[1] Journal of Medicinal Chemistry, 2010, vol. 53, # 3, p. 1250 - 1260
[2] Journal of the American Chemical Society, 1968, vol. 90, p. 7001 - 7007
3
[ 539-47-9 ]
[ 22515-16-8 ]
Reference：
[1] Journal of the American Chemical Society, 1968, vol. 90, p. 7001 - 7007
4
[ 147345-35-5 ]
[ 140-88-5 ]
[ 22515-16-8 ]
Reference：
[1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1994, # 8, p. 1111 - 1114
(0965) To a solution of <strong>[22515-16-8]diethyl 4,4-difluoroheptanedioate</strong> (4.3 g) in toluene (50 ml) was added potassium 2-methylpropan-2-olate (2.87 g) and the reaction stirred overnight at room temperature. The reaction was quenched with 1N aqueous HCl (100 ml) and extracted with diethyl ether (150 ml). The ether layer was washed with brine (50 ml), dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography (Reveleris 40 g) eluting with a gradient of 1% to 5% ethyl acetate/hexanes gave the title compound.
With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃;Cooling with ice;
General procedure: Solid, fine powdered lithiumaluminium hydride (2.0 - 5.0 equiv.) is suspended in dry THF at room temperature. The corresponding diacid- or diester derivative is dissolved in dry THF and the solution is slowly added dropwise to the lithiumaluminium slurry while cooling with an ice bath. After complete addition, the reaction solution is warmed to room temperature and the consumption of the starting material is checked by TLC. The suspension is carefully quenched with 2M H2SO4, additional water is added. For a better workup, the suspension should have a pH of ~7. The phases are separated and extracted with Et.20. The organic phase is washed with H2O, dried over MgSO4 and evaporated under reduced pressure. The crude product is directly used without further purification or purified via column chromatography using cyclohexane / tert. -butyl methyl ether. 1H NMR (500 MHz, CDCIs) delta 3.70 (t, 4H, J = 6.3 Hz), 2.00-1 .90 (m, 4H), 1 .79-1 .74 (m, 4H), 1 .38 (br s, 2H).
With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃;Cooling with ice;
General procedure: Solid, fine powdered lithiumaluminium hydride (2.0 - 5.0 equiv.) issuspended in dry THE at room temperature. The corresponding diacid- or diester derivative is dissolved in dry THE and the solution is slowly added dropwise to the lithiumaluminium slurry while cooling with an ice bath. After complete addition, the reaction solution is warmed to room temperature and the consumption of the starting material is checked by TLC. Thesuspension is carefully quenched with 2M H2504, additional water is added. Eor a better workup, the suspension should have a pH of -7. The phases are separated and extracted with Et20. The organic phase is washed with H20, dried over Mg504 and evaporated under reduced pressure. The crude product is directly used without further purification or purified via column chromatography using cyclohexane/tert-butyl methyl ether
7-ethoxy-4,4-difluoro-7-oxoheptanoic acid[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
65%
With ethanol; potassium hydroxide; at 0 - 20℃; for 10.0h;
A solution of diester (5.00 g, 19.8 mmol) in ethanol was cooled to 0 C; a solution of KOH (1 .22 g, 21 .8 mmol) in ethanol was added slowly to the reaction mixture. The resulting solution was warmed to rt and stirred for 10 h. The reaction mixture was coned, diluted with water, and extracted with hexanes:EA (3: 1 ). Tire aq phase was acidified with IN HC1 and extracted by EA. Tire organic phases were combined and dried over NarSOr, filtered, and coned to afford 2.88 g of the title compd as a white solid (65% yield). LCMS (ESI+): m/z = 225.21 | M 1 1 [ .
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