Methyl Acrylate → HCID 86629705, compound

HRID 384588Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][CH2:4][Si:5]([O:10][CH3:11])([O:8][CH3:9])[O:6][CH3:7].[C:12]([O:16][CH3:17])(=[O:15])[CH:13]=[CH2:14]>CO>[CH3:17][O:16][C:12]([CH2:13][CH2:14][N:1]([CH2:2][CH2:3][CH2:4][Si:5]([O:10][CH3:11])([O:6][CH3:7])[O:8][CH3:9])[CH2:14][CH2:13][C:12]([O:16][CH3:17])=[O:15])=[O:15]

Participants

Conditions

Temperature: 30 °C

Procedure

3-Aminopropyltrimethoxysilane (11.05 g, 61.7 mmol) and methanol (20 ml) are stirred together for 30 minutes at room temperature. To the mixture is added 41.46 g (482 mmol) of methyl acrylate. The reaction mixture is heated overnight in a 30° C. oil bath. The reaction mixture is concentrated at reduced pressure to give 21.50 g of crude methyl 3-[(2-methoxycarbonylethyl)-(3-trimethoxysilylpropyl)amino]propionate, a yellow viscous oil. A mixture of the crude product, 1-[4-(2-hydroxyethyoxy)phenyl]-2-hydroxy-2-methylpropan-1-one (26.85 g, 119.7 mmol) and 1,2-dimethoxyethane (80 ml) is heated in an oil bath at 85° (bath temperature). Zirconium(IV) acetylacetonate (1.16 g, 2.38 mmol) is added, and the mixture is stirred at 85° C. overnight and then at room temperature for 24 hours. Solvent is evaporated, and approximately one-half of the crude product is passed through a silica gel column with 5:1 chloroform:methanol as eluent to obtain 15.74 g of the title compound, a yellow semisolid product.

Workup

concentrationThe reaction mixture is concentrated at reduced pressure

Sources & evidence

ORD record: ord-3d310f7f5cf34887a800a91b4fd5aa38
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367743B2

Reaction notes

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