Pyridine → Acetoxymethyl 2-methacryloyloxyethyl Carbonate

HRID 1900153Notes

Reaction equation

HRID 1900153 reaction equation
Cl[C:2]([O:4][CH2:5][O:6][C:7](=[O:9])[CH3:8])=[O:3].[C:10]([O:15][CH2:16][CH2:17][OH:18])(=[O:14])[C:11]([CH3:13])=[CH2:12].N1C=CC=CC=1>C(Cl)Cl>[C:2](=[O:3])([O:18][CH2:17][CH2:16][O:15][C:10](=[O:14])[C:11]([CH3:13])=[CH2:12])[O:4][CH2:5][O:6][C:7](=[O:9])[CH3:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 133602-Hydroxyethyl MethacrylateHCID 14800978[(Chlorocarbonyl)oxy]methyl acetate

Product 1

HCID 23371997Acetoxymethyl 2-methacryloyloxyethyl CarbonateYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of acetoxymethyl chloroformate (1.00 g, 0.0066 mol) and 2-hydroxyethyl methacrylate (0.86 g, 0.0066 mol) in methylene chloride (30 ml), pyridine (0.52 g, 0.0066 mol) was added at 0° C. After 10 min at 0° C. and 18 hours at 25° C. the reaction mixture was washed with aqueous hydrochloric acid (100 ml), aqueous saturated sodium hydrogen carbonate (100 ml) and water (100 ml). The solvent was removed under reduced pressure after drying (MgSO4). Flash chromatography (silicagel, hexane/ethyl acetate (3:2)) gave 1.05 g (65%) of the title product.

Workup

  1. wash18 hours at 25° C. the reaction mixture was washed with aqueous hydrochloric acid (100 ml), aqueous saturated sodium hydrogen carbonate (100 ml) and water (100 ml)
  2. customThe solvent was removed under reduced pressure
  3. dry with materialafter drying (MgSO4)

Sources & evidence

ORD record
ord-fe29a4ad2aac47ca96e5083470ee6ca4
Source dataset
uspto-grants-1996_11
Patent number
US05574097

Reaction notes

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