Potassium Carbonate → 2-[2-(Tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-chloro-benzaldehyde

HRID 1806873Notes

Reaction equation

HRID 1806873 reaction equation
[Cl:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:18][CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]>CN(C)C=O.C(OCC)(=O)C>[C:24]([Si:21]([CH3:23])([CH3:22])[O:20][CH2:19][CH2:18][O:10][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:9][C:6]=1[CH:7]=[O:8])([CH3:27])([CH3:26])[CH3:25]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 124815-Chloro-salicylaldehydeHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

Product 1

HCID 575659162-[2-(Tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-chloro-benzaldehydeYield 94.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Step A To a solution of 5-chlorosalicylaldehyde (2 g, 12.8 mmol) (Aldrich) in N,N-dimethylformamide (40 mL) was added K2CO3 (5.3 g, 38 mmol), and (2-bromo-ethoxy)-tert-butyl-dimethyl-silane (3.67 g, 15 mmol, Aldrich). The reaction mixture was heated at 60° C. for 18 h. The crude was cooled to room temperature, diluted with ethyl acetate, washed with water, brine. The organic layer was separated, concentrated, and the residue was purified by chromatography (EtOAc:Hexanes=1:8, then 1:4) to give 2-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-chloro-benzaldehyde as a brown oil (Yield 3.8 g, 91%).

Workup

  1. temperatureThe crude was cooled to room temperature
  2. washwashed with water, brine
  3. customThe organic layer was separated
  4. concentrationconcentrated
  5. customthe residue was purified by chromatography (EtOAc

Sources & evidence

ORD record
ord-6c6c6e3a0db04605b2fea5e748b21030
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

Loading…