Methyl Acrylate → 2-[Hydroxy-(2-methyl-pyrimidin-5-yl)-methyl]acrylic acid methyl ester

HRID 474750ノート

反応式

HRID 474750 の反応式
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][N:3]=1.C1N2CCN(CC2)C1.[C:18]([O:22][CH3:23])(=[O:21])[CH:19]=[CH2:20]>O1CCOCC1.O.[Cl-].[Na+].O>[CH3:23][O:22][C:18](=[O:21])[C:19]([CH:8]([OH:9])[C:5]1[CH:4]=[N:3][C:2]([CH3:1])=[N:7][CH:6]=1)=[CH2:20]

参加物

7

反応物 3

HCID 7294Methyl AcrylateHCID 9237DabcoHCID 31609702-Methylpyrimidine-5-carbaldehyde

生成物 1

HCID 677753262-[Hydroxy-(2-methyl-pyrimidin-5-yl)-methyl]acrylic acid methyl ester収率 83.4%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

A mixture of 2-methylpyrimidine-5-carbaldehyde (1 g, 8.18 mmol, 1 eq), DABCO (1 eq, 935 mg) and methyl acrylate (5 eq, 3.68 ml) dissolved in a 1,4-dioxane (40 ml/H2O (40 ml) mixture was stirred at room temperature for 2 hours. The mixture was then poured into 300 ml of brine and the organic substances were extracted with DCM (3 times, 300 ml was used in total). The gathered DCM layers were dried, the solvent was evaporated and the obtained crude oil was triturated with diethyl ether to afford 2-[hydroxy-(2-methyl-pyrimidin-5-yl)-methyl]acrylic acid methyl ester (1.58 g, yield=83.40%, purity=90%) in form of white powder. MS: [M+H]+=209.18 1H NMR (300 MHz; CDCl3) δ/ppm 2.72 (s, 3H), 3.61 (br.s., 1H), 3.75 (s, 3H), 5.58 (s, 1H), 5.97 (s, 1H), 6.43 (s, 1H) 8.64 (s, 2H)

後処理

  1. extractionthe organic substances were extracted with DCM (3 times, 300 ml was used in total)
  2. dry with materialThe gathered DCM layers were dried
  3. customthe solvent was evaporated
  4. customthe obtained crude oil
  5. customwas triturated with diethyl ether

出典と根拠

ORDレコード
ord-88acd195df7c4acb9af65d0dec3faf64
出典データセット
uspto-grants-2014_01
特許番号
US08637536B2

反応ノート

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