Sodium Iodide → Methyl 3-(2-(benzyloxy)-5-bromophenyl)-3-phenylpropanoate

HRID 227196

反応式

HRID 227196 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7](=[O:12])[CH2:6][CH:5]2[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:19](=O)([O-])[O-:20].[K+].[K+].Cl[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[I-].[Na+]>CO.CC(C)=O>[CH2:26]([O:8][C:9]1[CH:10]=[CH:11][C:2]([Br:1])=[CH:3][C:4]=1[CH:5]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:6][C:7]([O:20][CH3:19])=[O:12])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 29249736-Bromo-3,4-dihydro-4-phenyl-2H-1-benzopyran-2-one

生成物 1

HCID 21476697Methyl 3-(2-(benzyloxy)-5-bromophenyl)-3-phenylpropanoate収率 102.9%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 887Methanol溶媒

実験手順

6-Bromo-4-phenyl-3,4-dihydro-coumarine (290 g, 0.96 mole) was dissolved in a mixture of methanol (1 L) and acetone (1 L). To the above solution were added potassium carbonate (160 g, 1.16 mole), α-chlorotoluene (140 g, 1.1 mole) and sodium iodide (30 g, 0.47 mole), and the mixture was stirred under reflux for 3 h. The solution was concentrated by distillation, and the residue treated with water and extracted with diethyl ether. The ethereal layer was washed with water, saturated sodium carbonate solution and water, successively. The organic layer was dried over sodium sulfate, filtered and then evaporated to give 420 g (≈100%) of the title compound as a light yellow oil.

後処理

  1. temperatureunder reflux for 3 h
  2. concentrationThe solution was concentrated by distillation
  3. additionthe residue treated with water
  4. extractionextracted with diethyl ether
  5. washThe ethereal layer was washed with water, saturated sodium carbonate solution and water
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-7f6db4f2f8654539bef679b64303df3a
出典データセット
uspto-grants-2009_07
特許番号
USRE040851E1

関連ノート

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