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

HRID 459179Notes

Reaction equation

HRID 459179 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-00b484fca49049ea8832d6e65f416fdc
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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