Hydrochloric Acid → 3,4-Dimethoxy-5-triisopropylsilanyloxymethylbenzaldehyde

HRID 1698660Notes

Reaction equation

HRID 1698660 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:22][CH3:23])[C:5]([O:20][CH3:21])=[C:6]([CH:19]=1)[CH2:7][O:8][Si:9]([CH:16]([CH3:18])[CH3:17])([CH:13]([CH3:15])[CH3:14])[CH:10]([CH3:12])[CH3:11].C([Li])CCC.[CH:29](N1CCOCC1)=[O:30].Cl>C1COCC1.C(OCC)(=O)C>[CH3:23][O:22][C:4]1[CH:3]=[C:2]([CH:19]=[C:6]([CH2:7][O:8][Si:9]([CH:16]([CH3:18])[CH3:17])([CH:13]([CH3:15])[CH3:14])[CH:10]([CH3:12])[CH3:11])[C:5]=1[O:20][CH3:21])[CH:29]=[O:30]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 20417N-FormylmorpholineHCID 67097070(5-Bromo-2,3-dimethoxybenzyloxy)triisopropylsilaneHCID 178418339Butyllithium

Product 1

HCID 595168883,4-Dimethoxy-5-triisopropylsilanyloxymethylbenzaldehyde

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the 3.616 g of (5-bromo-2,3-dimethoxybenzyloxy)triisopropylsilane in 60 ml of THF there was added dropwise 3.6 ml of n-butyllithium (2.66 M, hexane solution) at −78° C. under a nitrogen atmosphere. After stirring for 15 minutes, 2 ml of N-formylmorpholine was added and the mixture was stirred at room temperature for 20 minutes. Next, 1N hydrochloric acid was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (2.605 g) as an oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 20 minutes
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationThe desiccating agent was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Sources & evidence

ORD record
ord-7b5d29de7f0b4591a4238941b2ce0c98
Source dataset
uspto-grants-2012_04
Patent number
US08163787B2

Reaction notes

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