Electric Literature of 23377-40-4, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.23377-40-4, name is 3-(Hexadecyloxy)propan-1-ol, molecular formula is C19H40O2, molecular weight is 300.52, as common compound, the synthetic route is as follows.
To a tetrahydrofuran (THF) (1 mL/mmol) solution of l,3-bis(cyclcohexyl) imidazolium tetrafluoroborate (ICyHBF4) salt (0.05 eq.) and molecular sieves (0.5g/mmol), under argon, is added tBuOK (0.9 eq.) and stirred for 10 min. Lipophilic alcohol (1 eq.) and dialkyl H-phosphonate (2 eq.) are added and the reaction stirred at room temperature for 24h. The reaction is quenched with a saturated solution of ammonium chloride (5 mL/mmol) and filtrate on celite. Ethylacetate (AcOEt) (10 mL/mmol) is added to the solution then the organic and aqueous layers are separated. Aqueous phase is then extracted with AcOEt (10 mL/mmol) and the combinated organic layers are evaporated under vaccum. The corresponding alkyl/lipophilic chain H-phosphonate is finally purified by chromatography on silica gel.Example 2 : Synthesis of Bn/HDP H-phosphonateCompound 1 is synthesized according to procedure 1.4. from dibenzylphosphite as reported by the scheme 1. Scheme 11H NMR (400 MHz, CDCl3) delta = 7.74 (s, 0.5H, H-P), 7.41-7.33 (m, 5H, HA1), 5.99 (s, 0.5H, H-P), 5.11 (d, J = 9.5 Hz, 3H, OCH3), 4.20-4.07 (m, 2Eta, P-O-CH2-CH2-CH2-O), 3.46 (t, J = 6.1Hz, 2H, P-O-CH2-CH2-CH2-O), 3.37 (t, J = 6.7 Hz, 2H, 0-CH2-CH2-(CH2)I3-CH3), 1.90 ( p, J = 6.2 Hz, 2H, P-O-CH2-CH2-CH2-O), 1.53 (p, J = 6.9 Hz, 2H, 0-CH2-CH2-(CH2) ?- CH3), 1.35-1.19 (m, 26H, 0-CH2-CH2-(CH2)^-CH3), 0.87 (t, J = 6.4 Hz, 3H, 0-CH2-CH2- 13C NMR (100 MHz, CDCl3) delta = 136.6, 128.7, 128.6, 127.9, 126.9 (CA1), 71.2 (0-CH2-CH2- (CH2)I3-CH3), 67.2 (2C, CH2-Ph), 66.3 (P-O-CH2-CH2-CH2-O), 63.1, 63.0 (P-O-CH2-CH2- CH2-O), 31.9, 30.6 (2C), 29.7, 29.6 (2C), 29.5, 29.3, 26.1, 22.7 (CH2-P, P-O-CH2-CH2-CH2- O, 0-CH2-CH2-(CH2)^-CH3), 14.1 (O-CH2-CH2-(CH2)13-CH3).3 ’11P NMR (162 MHz, CDCl3): delta = 10.05.
The chemical industry reduces the impact on the environment during synthesis 23377-40-4, I believe this compound will play a more active role in future production and life.
Reference:
Patent; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE D’ORLEANS; AGROFOGLIO, Luigi A.; ROY, Vincent; PRADERE, Ugo; WO2010/146127; (2010); A1;,
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