Imidazole → Methyl 5-acetoxy-2-tert-butyldimethylsilyloxymethyl-4-methoxyhydrocinnamate

HRID 1898762Notes

Reaction equation

HRID 1898762 reaction equation
[C:1]([O:4][C:5]1[C:6]([O:19][CH3:20])=[CH:7][C:8]([CH:17]=[O:18])=[C:9]([CH:16]=1)[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])(=[O:3])[CH3:2].N1C=CN=C1.[C:26]([Si:30](Cl)([CH3:32])[CH3:31])([CH3:29])([CH3:28])[CH3:27]>C(Cl)Cl.CCOCC.O>[C:1]([O:4][C:5]1[C:6]([O:19][CH3:20])=[CH:7][C:8]([CH2:17][O:18][Si:30]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:32])[CH3:31])=[C:9]([CH:16]=1)[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 23372351Methyl 5-Acetoxy-2-formyl-4-methoxyhydrocinnamate

Product 1

HCID 23372362Methyl 5-acetoxy-2-tert-butyldimethylsilyloxymethyl-4-methoxyhydrocinnamate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl 5-acetoxy-2-formyl-4-methoxyhydrocinnamate (3.31 g) and imidazole (2.42 g) in methylene chloride (25 ml) is added a solution of tert-butylchlorodimethylsilane (2.73 g) in methylene chloride (25 ml). The mixture is stirred at room temperature for about 60 minutes, diluted with ether and water, and the organic layer washed with water, brine, dried over magnesium sulfate, filtered and concentrated in vacuo to give the desired product.

Workup

  1. washthe organic layer washed with water, brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cf38f96581534566aa8c89c9a242ad2a
Source dataset
uspto-grants-1996_11
Patent number
US05571506

Reaction notes

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