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

HRID 459179
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HRID 459179 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 80507Methyl methoxyacetateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 202986464-(Benzyloxy)-3-methylbenzaldehyde

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-00b484fca49049ea8832d6e65f416fdc
출처 데이터셋
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07192982B2

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