4-Hydroxy-2-Methoxybenzaldehyde → 4-(3-(tert-Butyldimethylsilyloxy)propoxy)-2-methoxybenzaldehyde

HRID 2207080Notes

Reaction equation

HRID 2207080 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([O:10][CH3:11])[CH:3]=1.Br[CH2:13][CH2:14][CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].C(OC([O-])=O)([O-])=O.[K+].[K+]>CN(C=O)C.O>[Si:17]([O:16][CH2:15][CH2:14][CH2:13][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([O:10][CH3:11])[CH:3]=1)([C:20]([CH3:21])([CH3:22])[CH3:23])([CH3:19])[CH3:18]

Participants

6

Reactant 3

HCID 5195414-Hydroxy-2-MethoxybenzaldehydeHCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneHCID 86587255Potassium dicarbonate

Product 1

HCID 879447074-(3-(tert-Butyldimethylsilyloxy)propoxy)-2-methoxybenzaldehydeYield 99.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The mixture of 4-hydroxy-2-methoxybenzaldehyde (10.0 g), (3-bromopropoxy)-tert-butyldimethylsilane (25.0 g), and potassium dicarbonate (13.6 g) in DMF (100 mL) was stirred at RT for 5 h. The mixture was diluted with water and extracted with EtOAc. And the combined organic solutions were washed with water and brine, dried and concentrated. The residue was purified by silica gel chromatography eluting with hexane/EtOAc to give 21.3 g of the subtitle compound as a yellow oil [as a mixture with (3-bromopropoxy)-tert-butyldimethylsilane].

Workup

  1. extractionextracted with EtOAc
  2. washAnd the combined organic solutions were washed with water and brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with hexane/EtOAc

Sources & evidence

ORD record
ord-5554d1c6c29440be8df0d61233e95257
Source dataset
uspto-grants-2016_06
Patent number
US09376398B2

Reaction notes

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