Sodium Chloride → 2,6-Dichloro-4-[3-((tert-butyldimethylsilanyloxy))-2-(tert-butyldimethylsilanyloxymethyl)-propoxy)-benzaldehyde

HRID 1006472Notes

Reaction equation

HRID 1006472 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=[O:5].[Si:12]([O:19][CH2:20][CH:21]([CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH2:22]OS(C)(=O)=O)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.[Na+].[Cl-]>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:22][CH:21]([CH2:28][O:29][Si:30]([C:33]([CH3:34])([CH3:36])[CH3:35])([CH3:31])[CH3:32])[CH2:20][O:19][Si:12]([C:15]([CH3:16])([CH3:17])[CH3:18])([CH3:13])[CH3:14])[CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=[O:5]

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 5283822,6-Dichloro-4-hydroxybenzaldehydeHCID 11015147Methanesulfonic acid 3-(tert-butyldimethylsilanyloxy)-2-(tert-butyldimethylsilanyloxymethyl)propyl ester

Product 1

HCID 1317245862,6-Dichloro-4-[3-((tert-butyldimethylsilanyloxy))-2-(tert-butyldimethylsilanyloxymethyl)-propoxy)-benzaldehyde

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3.43 g (18 mmol) A1, 7.40 g (18 mmol) methanesulfonic acid 3-(tert-butyldimethylsilanyloxy)-2-(tert-butyldimethylsilanyloxymethyl)propyl ester (Kim, H. S., et al., J. Med. Chem. 44 (2001) 3092-3108), 3.72 g (27 mmol) potassium carbonate and 41 mg (0.15 mmol) 18-crown-6 were stirred in 40 ml dimethylformamide at 40° C. overnight. 600 ml ethyl acetate and 250 ml aqueous NaCl were added. The organic layer was washed four times with saturated aqueous NaCl (80 ml each), dried over sodium sulfate and evaporated to dryness. Column chromatography of the residue on SiGel (heptane/ethyl acetate 10:1) yielded 508 mg (27%) A26.

Workup

  1. washThe organic layer was washed four times with saturated aqueous NaCl (80 ml each)
  2. dry with materialdried over sodium sulfate
  3. customevaporated to dryness
  4. customColumn chromatography of the residue on SiGel (heptane/ethyl acetate 10:1) yielded 508 mg (27%) A26

Sources & evidence

ORD record
ord-37be19c42e71443ab924b3311253b6a8
Source dataset
uspto-grants-2004_09
Patent number
US06790852B2

Reaction notes

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