Reference of 81927-55-1, A common heterocyclic compound, 81927-55-1, name is Benzyl 2,2,2-trichloroacetimidate, molecular formula is C9H8Cl3NO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
(R)-Methyl 3-hydroxybutanoate (2.0 g, 17.0 mmol, 1.0 equiv) was stirred in cyclohexane(113 mL) and CH2Cl2 (56 mL) and benzyl 2,2,2-trichloroacetimidate (8.56 g, 33.9 mmol, 2.0 equiv) followed byTsOHH2O (10 mL, 0.85 mmol, 0.1 equiv) were added and the mixturestirred at 25 C for 18 h. Reactionwas quenched with saturatedaqueous NaHCO3 (100 mL) and the solution extracted with CH2Cl2(3100 mL), dried (MgSO4), rotary evaporated, and chromatographed(1:9 EtOAc/hexanes) to afford benzyl-protected alcohol 68(2.66 g, 76%) as a clear oil, which was used without further purification.Methyl ester 68 was stirred in NaOH (1 M, 22.0 mL,22.1 mmol, 1.8 equiv) and THF (20 mL) for 72 h. The mixture wasacidified to pH 3 using 1 M HCl, extracted with CH2Cl2 (3200 mL),the organic extracts combined, washed with brine (150 mL), dried(MgSO4), and rotary evaporated to afford carboxylic acid 69 (1.94 g,83%) as a clear oil: Rf 0.4 (1:9 MeOH/CH2Cl2); [a]D25 0.83 (c 0.113,CHCl3); IR (neat) nmax 3029 (br), 1706, 1454, 1377, 1305, 1204, 1134,1075 cm1; 1H NMR (500 MHz, C6D6) d 7.25e7.24 (m, 2H), 7.17e7.14(m, 2H), 7.08e7.05 (m, 1H), 4.27 (q, J13.0 Hz, 2H), 3.80e3.74 (m,1H), 2.44 (dd, J15.0, 7.0 Hz, 1H), 2.13 (dd, J15.0, 5.0 Hz, 1H), 0.96(d, J6.0 Hz, 3H); 13C NMR (125 MHz, C6D6) d 177.3, 139.1, 128.2(2C), 128.0, 127.8 (2C), 71.7, 70.8, 41.8, 19.6; HRMS (CI) calcd forC11H18NO, requires 212.1287, found 212.1297 (D4.7 ppm); Anal.Calcd for C11H14O3: C, 68.02; H, 7.27. Found: C, 68.13; H, 7.14.
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Article; Anderson, Katie; Laclef, Sylvain; Barrett, Anthony G.M.; Tetrahedron; vol. 70; 35; (2015); p. 5569 – 5579;,
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