Methacrylic Acid → HCID 86658984, compound

HRID 245131Notes

Reaction equation

HRID 245131 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][OH:10])=[CH:3][CH:2]=1.[C:11]([OH:16])(=[O:15])[C:12]([CH3:14])=[CH2:13].N1(C2C=CN=CC=2)CCCC1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][OH:10])=[CH:3][CH:2]=1.[C:11]([O-:16])(=[O:15])[C:12]([CH3:14])=[CH2:13]

Participants

6

Reactant 4

HCID 4093Methacrylic AcidHCID 10868DicyclohexylcarbodiimideHCID 729234-PyridinepropanolHCID 755674-Pyrrolidinopyridine

Product 1

HCID 86658984HCID 86658984, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After 6.85 g (50 mmol) of 4-pyridinepropanol (manufactured by Aldrich Co.) represented by formula (19), 4.73 g (55 mmol) of methacrylic acid (manufactured by Aldrich Co.) represented by formula (20), and 740 mg (5 mmol) of 4-(1-pyrrolidinyl)pyridine (manufactured by Aldrich Co.) were dissolved in 100 ml of dehydrated dichloromethane (manufactured by WAKO Co.), 11.3 g (55 mmol) of N,N′-dicyclohexylcarbodiimide (DCC) (manufactured by Aldrich Co.) was added thereto and allowed to react at room temperature for 1 hour. Then, insoluble urea was removed by filtration, followed by removal of solvent under reduced pressure. The residual material was purified by column chromatography (column: silica (manufactured by WAKO Co.), solvent: hexane/ethyl acetate) to obtain 4-pyridinepropanol-methacrylate represented by formula (21) (yield amount: 8.5124 g, yield rate: 82.8%). The reaction scheme is shown below.

Workup

  1. customto react at room temperature for 1 hour
  2. customThen, insoluble urea was removed by filtration
  3. customfollowed by removal of solvent under reduced pressure
  4. customThe residual material was purified by column chromatography (column: silica (manufactured by WAKO Co.), solvent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-1714f9febc124b72b63b2cfa38a36192
Source dataset
uspto-grants-2014_02
Patent number
US08658735B2

Reaction notes

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