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ChemicalBook CAS DataBase List 1-Chloroethyl cyclohexyl carbonate

1-Chloroethyl cyclohexyl carbonate synthesis

3synthesis methods
1-Chloroethyl cyclohexyl carbonate is mainly used in organic synthesis, perfume intermediates, can be used as candesartan cilexetil, cefotiam cilexetil and other pharmaceutical intermediates. It was prepared from Cyclohexy alcohol  and  1-Chloroethyl chloroformate by stirring in 1-Chloroethyl chloroformate with pyridine for overnight at room temperature.
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Yield:99464-83-2 94%

Reaction Conditions:

with pyridine in dichloromethane at 0 - 20;

Steps:

4
EXAMPLE 4 Synthesis of PGB-03 (3-Aminomethyl-5-methyl-hexanoic acid 1-cyclohexyloxycarbonyloxy-ethyl ester) Procedure: Cyclohexy alcohol (1.4 g, 13.97 mmol) was dissolved in CH2Cl2 (15 mL) under the treatment in a nitrogen atmosphere (0-5° C.). 1-Chloroethyl chloroformate (2.0 g, 13.97 mmol) and CH2Cl2 (10 mL) were slowly added. The solution was stirred for 15 minutes and pyridine (1.22 g, 15.42 mmol) and CH2Cl2(2 mL) were added dropwise. After stirring overnight at room temperature, CH2Cl2 (20 mL) and water (20 mL) were added to the reaction solution. The product was extracted to the CH2Cl2 phase and washed with water (3*20 mL). The residue was dried and concentrated to give 2.64 g of Carbonic acid cyclohexyl ester 1-chloro-ethyl ester 6 (Yield: 94%). 1H-NMR (CDCl3, 500 MHz) δ 1.22-1.30 (m, 1H), 1.32-1.41 (m, 2H), 1.42-1.58 (m, 3H), 1.71-1.80 (m, 2H), 1.83 (d, J=6.0 Hz, 3H), 1.89-2.00 (m, 2H), 4.65-4.72 (m, 1H), 6.43 (q, J=6.0 Hz, 1H).

References:

Hwang, Jenn-Tsang;Hwang, Chrong-Shiong;Chang, Yow-Lone;Yao, Chung-Niang US2008/125483, 2008, A1 Location in patent:Page/Page column 6-7

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