Triethylamine → 2-Hydroxyethyl Methacrylate

HRID 227364Notes

Reaction equation

HRID 227364 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4].C([O:18][CH2:19][CH2:20][O:21][C:22](=[O:26])[C:23]([CH3:25])=[CH2:24])(=O)CCC([O-])=O.C(N(CC)CC)C>C(OCC)(=O)C>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4].[CH3:25][C:23]([C:22]([O:21][CH2:20][CH2:19][OH:18])=[O:26])=[CH2:24]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27735202H-Pyran-4-carboxylic acid, tetrahydro-, methyl esterHCID 21903814HCID 21903814, compound

Product 2

HCID 133602-Hydroxyethyl MethacrylateHCID 27735202H-Pyran-4-carboxylic acid, tetrahydro-, methyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A 1 L three neck flask equipped with a mechanical stirrer, condenser, thermocouple, and addition funnel was charged with THPE GE (112.5 g), mono-2-(methacryloyloxy)ethyl succinate (218.3 g), triethylamine (1.2 g), and Prostab® 5415 (0.2 g). The mixture was heated to 80° C. for 7.5 hr to obtain a pale yellow mixture. The mixture was dissolved in 1250 mL of ethyl acetate, extracted with 500 mL of water followed by 500 mL of saturated sodium bicarbonate solution. The solution was dried with anhydrous sodium sulphate, then added to 1 liter of silica gel (Merck silica gel 60), and the solvent was removed. The silica gel containing the compound was then added to a column with 2500 g of silica gel and was eluted with a mixture of hexanes and ethyl acetate to isolate a purified fraction of the desired compound, THPE GE Su HEMA. 1H NMR (500 MHz, CDCl3) Δ1.93 (s, 9H), 2.08 (s, 3H), 2.61-2.7 (m, 12H), 3.8-4.2 (m, 15H), 4.3-4.4 (m, 12H), 5.6 (m, 3H), 6.1 (m, 3H), 6.75 (m, 6H), 6.98 (m, 6H).

Workup

  1. additionthermocouple, and addition funnel
  2. customto obtain a pale yellow mixture
  3. extractionextracted with 500 mL of water
  4. dry with materialThe solution was dried with anhydrous sodium sulphate
  5. additionadded to 1 liter of silica gel (Merck silica gel 60)
  6. customthe solvent was removed
  7. additionThe silica gel containing the compound was then added to a column with 2500 g of silica gel
  8. washwas eluted with a mixture of hexanes and ethyl acetate

Sources & evidence

ORD record
ord-b5078d28cb9a4ac7ac971a4e8be94c53
Source dataset
uspto-grants-2009_07
Patent number
US07560500B2

Reaction notes

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