Reference of 17205-02-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 17205-02-6 name is Ethyl 3-hydroxycyclobutanecarboxylate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.
[0729] To a solution of ethyl 3-hydroxycyclobutanecarboxylate (10.2 g, 78.4 mmol) in dry pyridine (56.5 mL) at ooC., TsCI (14.9 g, 78.4 mmol) was added portionwise. Theresulting mixture was stirred at rt overnight. The reactionmixture was concentrated under reduced pressure and theresidue obtained was dissolved in EtOAc (100 mL) andsequentially washed with 2 N HCI (100 mL), saturatedNaHC03 (100mL)andwater(100mL). TheEtOAclayerwasdried over Na2S04 , filtered, and concentrated to obtain ethyl3-(tosyloxy)cyclobutanecarboxylate as a pale yellow oil,which was used in the next step without further purification.[0730] To a solution ethyl 3-(tosyloxy)cyclobutanecarboxylate (6.0 g, 20 mmol, as prepared above) in anhydrousMEK(20mL), Nal (7.5 g, 50mmol)was added. Theresultingmixture was heated at 120 C. for 4 h in a microwave reactor.The reaction mixture was concentrated and water (50 mL)was added. The resultant mixture was extracted with ether(100mL) and washed with 10% Na2 S 20 3 (50mL) and water(50 mL). The ether layer was separated, dried over Na2S04 ,filtered, and concentrated. The residue was distilled underreduced pressure to obtainthe title compound 43a as a cis andtrans mixture. 1 H-NMR (400 MHz, CDCI 3 ) o (ppm): 4.66(quin, 1=7.2 Hz, lH), 4.30-4.48 (m, 2H), 4.02-4.24 (m, 6H),3.30-3.49 (m, lH), 3.03-3.21 (m, 2H), 2.64-3.02 (m, 12H),1.18-1.34 (m, 9H).
At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 3-hydroxycyclobutanecarboxylate, and friends who are interested can also refer to it.
Reference:
Patent; JANSSEN PHARMACEUTICA, NV; Player, Mark R.; Meegalla, Sanath K.; Illig, Carl R.; Chen, Jinsheng; Wilson, Kenneth J.; Lee, Yu-Kai; Parks, Daniel J.; Huang, Hui; Patel, Sharmila; Lu, Tianbao; US2014/364414; (2014); A1;,
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