Pyridine → 1-Chloroethyl 2-methacryloyloxyethyl carbonate

HRID 1938116Notes

Reaction equation

HRID 1938116 reaction equation
N1C=CC=CC=1.Cl[C:8]([O:10][CH:11]([Cl:13])[CH3:12])=[O:9].[C:14]([O:19][CH2:20][CH2:21][OH:22])(=[O:18])[C:15]([CH3:17])=[CH2:16]>ClCCl>[C:8](=[O:9])([O:22][CH2:21][CH2:20][O:19][C:14](=[O:18])[C:15]([CH3:17])=[CH2:16])[O:10][CH:11]([Cl:13])[CH3:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 133602-Hydroxyethyl MethacrylateHCID 5213051-Chloroethyl chloroformate

Product 1

HCID 544861711-Chloroethyl 2-methacryloyloxyethyl carbonateYield 74.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Pyridine (0.89 ml, 11.00 mmol) is added dropwise to a solution of 1-chloroethyl chloroformate (1.20 ml, 11.00 mmol) and 2-hydroxyethyl methacrylate (1.22 ml, 10.00 mmol) in dichloromethane (12 ml) at 3° C. under a dry N2 atmosphere. After 15 min. at 3° C. and 17 hours at 20° C. the reaction mixture is transferred to a separating funnel with the aid of dichloromethane (10 ml). The reaction mixture is washed with hydrochloric acid (1.00M, 10 ml), saturated aqueous sodium hydrogen carbonate (10 ml) and water (2×10 ml). The organic phase is dried (MgSO4) and the solvent evaporated under reduced pressure to give 1.76 g (74%) of the title product. 1H NMR (60 MHz, CDCl3): δ1.85 (3H, d, J=6 Hz, CH3 --CH), 1.96 (3H, d, J=2 Hz, CH3 --C=), 5.55 (1H, m, CH=), 6.10 (1H, m, CH=), 6.38 (1H, k, J=6 Hz, CH--CH3).

Workup

  1. washThe reaction mixture is washed with hydrochloric acid (1.00M, 10 ml), saturated aqueous sodium hydrogen carbonate (10 ml) and water (2×10 ml)
  2. dry with materialThe organic phase is dried (MgSO4)
  3. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-e027c3e815304f1e8ffff5e076a06cdb
Source dataset
uspto-grants-1997_12
Patent number
US05693321

Reaction notes

Loading…