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ChemicalBook CAS DataBase List 1-Methylcyclobutanol

1-Methylcyclobutanol synthesis

11synthesis methods
-

Yield: 99%

Reaction Conditions:

in diethyl ether at 0; for 3 h;

Steps:

214 1-methylcyclobutanol
To a solution of cyclobutanone (5 g, 71.3 mmol) in diethyl ether (400 mL) at 0°C was added dropwise 3M MeMgBr/diethyl ether (47.6 mL, 143 mmol) and the resulting mixture was stirred for 3 h at 0°C. Then, the reaction mixture was poured over cooled iN HC1 and extracted twice with ether, dried (Na2SO4), filtered and concentrated to afford 1- methylcyclobutanol (6.1 g, 70.8 mmol, 99 % yield) as colorless oil. ‘H NMR (500MHz, CDCl3) 2.17 - 1.97 (m, 4H), 1.90 - 1.67 (m, 2H), 1.61 - 1.47 (m, 1H), 1.39 (t, J=0.8 Hz, 3H).

References:

BRISTOL-MYERS SQUIBB COMPANY;NAIDU, B. Narasimhulu;PATEL, Manoj;D'ANDREA, Stanley;ZHENG, Zhizhen Barbara;CONNOLLY, Timothy P.;LANGLEY, David R.;PEESE, Kevin;WANG, Zhongyu;WALKER, Michael A.;KADOW, John F. WO2014/28384, 2014, A1 Location in patent:Page/Page column 213