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ChemicalBook CAS DataBase List (R)-1-(3-Chlorophenyl)-2-hydroxy-1-propanone
291275-46-2

(R)-1-(3-Chlorophenyl)-2-hydroxy-1-propanone synthesis

6synthesis methods
-

Yield:291275-46-2 87%

Reaction Conditions:

with methanesulfonamide;1,4-bis(9-O-dihydroquinidine)phthalazine in water;tert-butyl alcohol at 0; for 16 h;

Steps:

2

Step 2: (i~)-l-(3-ChIorophenyl)-2-hydroxypropan-l-one ((/~)- 10a).; A mixture of AD-mix-β (50.6 g) and CH3S02NH2 (3.5 g, 0.037 mol) in fert-butyl alcohol-water (120 mL/120 mL) was cooled at 0 °C and treated with 9a (10 g, 0.036 mol). The reaction mixture was stirred for 16 h at 0 °C. Sodium sulfite (36 g) was added and the mixture was stirred for another hour. The mixture was filtered through a Celite pad and washed with ether. The filtrate was transferred to a separation funnel and the lower dark colored layer was discarded. The upper yellowish phase was separated, dried (Na2S04), filtered, and concentrated. The crude product was purified by column chromatography on silica gel using hexanes-EtOAc (10: 1 to 3: 1) as the eluent to give 5.8 g (87%) of title product as light greenish oil: [a]20D +64.2° (c 1.2, CHC13); 1H NMR (CDC13) δ 7.91 (s, 1H), 7.80 (d, 1H, J = 7.8 Hz), 7.62-7.57 (m, 1H), 7.46 (t, 1H, J = 7.8 Hz), 5.15-5.08 (m, 1H), 3.68-3.65 (m, 1H), 1.45 (d, 3H, J - 7.1 Hz). C9H iC102. Characterization data is similar to that reported in Fang, Q. K. et al, Tetrahedron: Asymmetry 2000, 11 : 3659-3663.

References:

WO2011/146821,2011,A2 Location in patent:Page/Page column 54