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HRID 1249958作成日:2026年10月27日

Triethylamine → 2-methoxy-4-[(E)-2-methoxycarbonyl-vinyl]-phenyl 4-[6-(2-methyl-acryloyloxy)-hexyloxy]-benzoate

https://huagongshe.com/reaction/1249958

反応式

関与物質

役割名称HCID仕込み量
反応物TriethylamineHCID 8471—
反応物Methyl 4-hydroxy-3-methoxy-cinnamateHCID 16830—
反応物Thionyl ChlorideHCID 24386—
反応物4-[6-(2-Methyl-acryloyloxy)-hexyloxy]-benzoateHCID 7021645—
触媒DimethylformamideHCID 6228—
溶媒TetrahydrofuranHCID 8028—
生成物2-methoxy-4-[(E)-2-methoxycarbonyl-vinyl]-phenyl 4-[6-(2-methyl-acryloyloxy)-hexyloxy]-benzoateHCID 1832918350.8%

反応条件

温度90 °C

反応手順

8.5 g (0.028 mol) of 4-[6-(2-methyl-acryloyloxy)-hexyloxy]-benzoate were treated with 6 ml of thionyl chloride and 3 drops of DMF and the mixture was heated to 90° C. for 2 hours. The excess thionyl chloride was completely removed firstly in a water-jet vacuum and subsequently in a high vacuum. The residual acid chloride was taken up in 20 ml of dichloromethane and slowly added dropwise at 0° C. to a solution of 5.25 g (0.025 mol) of methyl 4-hydroxy-3-methoxy-cinnamate and 4.25 ml of triethylamine in 25 ml of THF. The batch was stirred at room temperature overnight, filtered and the filtrate was evaporated to dryness. The residue was purified by column chromatography on silica gel with dichloromethane/diethyl ether (19:1) and subsequently by recrystallization from ethanol/THF. 6.31 g of 2-methoxy-4-[(E)-2-methoxycarbonyl-vinyl]-phenyl 4-[6-(2-methyl-acryloyloxy)-hexyloxy]-benzoate were isolated as a white powder; m.p. 92-94° C.

情報源と証拠

DOI10.6084/m9.figshare.5104873.v1
特許番号US06335409B1
出典データセットuspto-grants-2002_01
ORD IDord-2503be71934b4182838359b3d2eb075a
出典メモuspto-grants-2002_01