1-Chloroethyl 1-methylethyl carbonate

a solution of 2-propanol (0.64 mL, 8.39 mmol) and pyridine (0.79 mL, 9.79 mmol) at -78°C was added 1-chloroethyl chlorofonnate (0.76 mL, 6.99 mmol) dropwise. The reaction mixture was allowed to slowly warm to room temperature and stir overnight. The reaction mixture became a solid white clump and was sonicated in dichloromethane. The resulting suspension was concentrated and the white solid was dissolved in ethyl acetate and washed with water and brine. The organics were dried over magnesium sulfate, filtered and concentrated to afford the title compound as a colorless liquid, 1.29 g, 99percent.‘H NMR (300 MHz, CDCl3 ö: 1.35 (m, 6H); 1.84 (d, 3H); 4.96 (m, 1H); 4.44 (m, 1H).PREPARATION 46; 1-Chloroethyl isopropyl carbonate; To a solution of isopropanol (1.09 g, 18.27 mmol) and pyridine (1.45 g, 18.35 mmol) in of dichloromethane (30 ml) at-78 °C was dropwise added (10 minutes) 1-chloroethyl chloroformate (2.66 g, 18.60 mmol) under argon. After the addition, the cooling bath was removed and the mixture was allowed to warm to rt and stirred at that temperature overnight. The reaction was diluted with additional dichloromethane (20 ml), washed with brine and dried over anhydrous sodium sulfate. Removal of the solvent under reduced pressure afforded the title compound as a colourless oil (3 g, 97percent yield). No. (CDCl3): 1.33 (d, 3H), 1.35 (d, 3H), 1.84 (d, 3H), 4.95 (m, 1H), 6.43 (q, 1H).0.66 g of isopropanol was added to 1.43 g of 1-chloroethyl chloroformate, and the solution was cooled to 0° C. in an ice-water bath. The mixture of 0.84 g of pyridine and 10 ml ethyl ether was added dropwise into the solution. The solution was reacted for 1 hour at that temperature, following 4 hours at room temperature. The reaction was stopped and the mixture was filtered, and the filtrate was washed respectively with 10percent hydrochloric acid and water once. The organic phase was dried and concentrated to give 1.461 g of a light yellow liquid 1-chloroethyl isopropyl carbonate with a yield of 87.7percent. The crude was directly used in the next reaction without purification.The compound 1-chloroethyl chloroformate (3 ml, 27.8 mmol) was diluted with DCM (25 ml)Cooled to 0 ° C, Isopropanol (2.1 ml, 27.8 mmol) diluted with DCM (25 ml) was slowly added with a constant pressure dropping funnel, Reaction about 15min, Pyridine (2.4 ml, 30.6 mmol) diluted with DCM (5 ml) was added slowly using a constant pressure dropping funnel, The process to keep the same low temperature, After adding, Reaction at room temperature overnight, Then diluted with water, Extracted with DCM, Organic phase dry, After concentration of 3.74g light yellow liquid, The yield was 81percent.Preparation : Preparation of 1 -iodoethyl isopropylcarbonate(1) ; Preparation of 1-chloroethyl isopropylcarbonate 1-Chloroethyl chloroformate (31.7 g, 0.22 mol) was dissolved in methylene chloride (200 ml), and isopropanol (39.7 ml, 0.52 mol) was added thereto while ice-cooling. Pyridine (23 ml, 0.28 mol) was slowly added to the reaction mixture over 15 minutes. The reaction mixture was slowly heated to room temperature and then stirred for 30 minutes. The reaction mixture was sequentially washed with water, 5percent brine, and 5percent potassium hydrogen sulfate solution, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was distilled under a reduced pressure to obtain 25 g of 1-chloroethyl isopropylcarbonate (yield: 68percent). bpδδmmHg: 92-94 To a solution of 1-Chloroethyl chloroformate (step-1, 3.5 g, 24.4 mmol, 1.0 eq) in CH

Molecular Weight:166.60
XLogP3:2.4
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:166.0396719
Monoisotopic Mass:166.0396719
Topological Polar Surface Area:35.5
Heavy Atom Count:10
Complexity:114
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes