Benzaldehyde, 4-(phenylmethoxy)- → (E)-Ethyl 3-(4-(benzyloxy)phenyl)-2-methylacrylate

HRID 62837

反応式

HRID 62837 の反応式
[C:1]([CH2:6][CH:7]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:3][CH2:4][CH3:5])=[O:2].[CH2:27]([O:34][C:35]1[CH:42]=[CH:41][C:38]([CH:39]=O)=[CH:37][CH:36]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1COCC1>[CH2:4]([O:3][C:1](=[O:2])/[C:6](/[CH3:7])=[CH:39]/[C:38]1[CH:41]=[CH:42][C:35]([O:34][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:36][CH:37]=1)[CH3:5]

参加物

4

反応物 2

HCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 12607919Ethyl 3-(triphenyl-lambda~5~-phosphanylidene)propanoate

生成物 1

HCID 12235562(E)-Ethyl 3-(4-(benzyloxy)phenyl)-2-methylacrylate収率 97.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Carbethoxyethylidene triphenylphosphorane (1.02 g, 2.81 mmol) was dissolved in anhydrous THF (25 mL), and 4-benzyloxy-benzaldehyde (0.5 g, 2.36 mmol)/THF (10 mL) solution was added dropwise thereto at −78° C. The mixture was heated slowly to room temperature and then stirred for 12 hours. After the termination of the reaction, the reactant was concentrated under reduced pressure. The residue was added with water and then extracted with EtOAc. The organic layer was dried with MgSO4 and purified by column chromatography (eluent, EtOAc/Hex=1/9) to obtain the title compound (0.68 g, 97.4%).

後処理

  1. customat −78° C
  2. customAfter the termination of the reaction
  3. concentrationthe reactant was concentrated under reduced pressure
  4. additionThe residue was added with water
  5. extractionextracted with EtOAc
  6. dry with materialThe organic layer was dried with MgSO4
  7. custompurified by column chromatography (eluent, EtOAc/Hex=1/9)

出典と根拠

ORDレコード
ord-76ce6663f0764a9fa978df089572bfa1
出典データセット
uspto-grants-2016_09
特許番号
US09447044B2

関連ノート

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