Water → 3-Chloro-4-(2-trimethylsilylethoxymethoxy)benzaldehyde

HRID 132680Notes

Reaction equation

HRID 132680 reaction equation
[Cl:1][C:2]1[C:3]([OH:10])=[CH:4][CH:5]=[C:6]([CH:9]=1)[CH:7]=[O:8].C(N(C(C)C)CC)(C)C.[CH3:20][Si:21]([CH3:28])([CH3:27])[CH2:22][CH2:23][O:24][CH2:25]Cl.O>C(Cl)Cl>[Cl:1][C:2]1[CH:9]=[C:6]([CH:5]=[CH:4][C:3]=1[O:10][CH2:25][O:24][CH2:23][CH2:22][Si:21]([CH3:28])([CH3:27])[CH3:20])[CH:7]=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 170223-Chloro-4-hydroxybenzaldehydeHCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 865914053-Chloro-4-(2-trimethylsilylethoxymethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5 g (31.93 mmol) of 5-chloro-4-hydroxybenzaldehyde are dissolved in 300 ml of methylene chloride and 6.7 ml (38.3 mmol) of N,N-diisopropyl-N-ethylamine and 5.9 ml (33.52 mmol) of 2-trimethylsilylethoxymethyl chloride (SEMCl) are added to this at 0° C. The mixture is allowed to return to room temperature and stirred overnight. Water is then added and the mixture is extracted with methylene chloride. The organic phase is dried and the solvent is evaporated off. The product of the title is obtained, which is purified by chromatography on a silica gel column, eluting with a 95/5 and then 9/1 heptane/ethyl acetate mixture.

Workup

  1. customto return to room temperature
  2. extractionthe mixture is extracted with methylene chloride
  3. customThe organic phase is dried
  4. customthe solvent is evaporated off
  5. customThe product of the title is obtained
  6. customwhich is purified by chromatography on a silica gel column
  7. washeluting with a 95/5

Sources & evidence

ORD record
ord-5495e7bd39314462a56df78bc1cb3c03
Source dataset
uspto-grants-2008_06
Patent number
US07388031B2

Reaction notes

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