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Potassium Carbonate → Methyl 2-[(4-{2-[benzyl(hexyl)amino]-2-oxoethyl}-2-methoxyphenoxy)methyl]benzoate

HRID 2111992
ノート
印刷プレビュー

反応式

HRID 2111992 の反応式
[CH2:1]([N:8]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:9](=[O:20])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([O:18][CH3:19])[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][O:28][C:29](=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH2:36]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([N:8]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:9](=[O:20])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:36][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[C:29]([O:28][CH3:27])=[O:38])=[C:13]([O:18][CH3:19])[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 2734813Methyl 2-(bromomethyl)benzoateHCID 68872097N-Benzyl-N-hexyl-2-(4-hydroxy-3-methoxyphenyl)acetamide

生成物 1

HCID 68870229Methyl 2-[(4-{2-[benzyl(hexyl)amino]-2-oxoethyl}-2-methoxyphenoxy)methyl]benzoate収率 86%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

N-Benzyl-N-hexyl-2-(4-hydroxy-3-methoxyphenyl)acetamide (84 mg, 0.236 mmol), 2-bromomethylbenzoic acid methyl ester (57 mg, 0.248 mmol) and potassium carbonate anhydrous (49 mg, 0.355 mmol) were mixed in acetonitrile (5 ml). The mixture was heated to reflux overnight and then evaporated to dry. Ethyl acetate and water were added and the two phases were separated. The organic phase was washed with brine and dried (magnesium sulphate) and evaporated. Chromatography of the residue on a column (ISOLUTE® SI, 2 g/6 ml) using DCM, MeOH/DCM (0.5:99.5) as eluant gave 102 mg the desired product yield 86%.

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customevaporated
  4. customto dry
  5. additionEthyl acetate and water were added
  6. customthe two phases were separated
  7. washThe organic phase was washed with brine
  8. dry with materialdried (magnesium sulphate)
  9. customevaporated

出典と根拠

ORDレコード
ord-be953b7e4db6404abc396560a2f614ad
出典データセット
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07521461B2

反応ノート

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