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Methyl methoxyacetate → 3-(4-Benzyloxy-3-methyl-phenyl)-3-hydroxy-2-methoxy-propionic acid ethyl ester

HRID 459179
ノート
印刷プレビュー

反応式

HRID 459179 の反応式
[CH3:1][Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:11]([O:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][C:20]=1[CH3:27])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH3:28][O:29][C:30](=[O:34])[CH2:31][O:32][CH3:33]>C1COCC1>[CH2:28]([O:29][C:30](=[O:34])[CH:31]([O:32][CH3:33])[CH:23]([C:22]1[CH:25]=[CH:26][C:19]([O:18][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:20]([CH3:27])[CH:21]=1)[OH:24])[CH3:1]
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 80507Methyl methoxyacetateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 202986464-(Benzyloxy)-3-methylbenzaldehyde

生成物 1

HCID 694224223-(4-Benzyloxy-3-methyl-phenyl)-3-hydroxy-2-methoxy-propionic acid ethyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of NaHMDS (1.1 eq) in dry THF at −78° C. a mixture of 4-Benzyloxy-3-methyl-benzaldehyde (1 eq) and Methoxy-acetic acid methyl ester (1.25 eq) in THF were added dropwise and the mixture reaction at this temperature over 1.5 hours. Then the reaction was quenched with HCl 3N and allowed to rise room temperature. Washed with brine and extracted with ether. The organic layer was dried and concentrated to dryness to give after chromatography in silica gel the title product.

後処理

  1. additionwere added dropwise
  2. customthe mixture reaction at this temperature over 1.5 hours
  3. customThen the reaction was quenched with HCl 3N
  4. customto rise room temperature
  5. washWashed with brine
  6. extractionextracted with ether
  7. customThe organic layer was dried
  8. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-00b484fca49049ea8832d6e65f416fdc
出典データセット
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07192982B2

反応ノート

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