Triethylsilane → HCID 53648849, compound

HRID 234227Notes

Reaction equation

HRID 234227 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C:4]1[C:9]([CH:10]=O)=[C:8]([O:12][Si:13]([CH3:21])([CH3:20])[C:14]([CH3:19])([CH3:18])[CH:15]([CH3:17])[CH3:16])[CH:7]=[C:6]([O:22][CH3:23])[C:5]=1[F:24].C([SiH](CC)CC)C>FC(F)(F)C(O)=O.ClCCl>[CH3:1][O:2][C:3](=[O:25])[C:4]1[C:9]([CH3:10])=[C:8]([O:12][Si:13]([CH3:20])([CH3:21])[C:14]([CH3:19])([CH3:18])[CH:15]([CH3:16])[CH3:17])[CH:7]=[C:6]([O:22][CH3:23])[C:5]=1[F:24]

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 53833163HCID 53833163, compound

Product 1

HCID 53648849HCID 53648849, compoundYield 87.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 1.3 g of 2-fluoro-6-formyl-3-methoxy-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-benzoic acid methyl ester in 4 ml of trifluoroacetic acid, cooled to 0° C., was added over 10 min a solution of 0.6 g of triethylsilane in 4 ml of dichloromethane. The solution was kept at 0° C. for 18 h and then evaporated in vacuo. The residue was taken up in ethyl acetate and the solution was successively washed with water, saturated sodium carbonate solution and brine, and dried over sodium sulfate. The solvent was evaporated in vacuo and the residue was chromatographed on silica gel using ethyl acetate/hexane (1:3, v/v) as eluent to yield 1.1 g of 2-fluoro-3-methoxy-6-methyl-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]benzoic acid methyl ester as colorless oil.

Workup

  1. customevaporated in vacuo
  2. washthe solution was successively washed with water, saturated sodium carbonate solution and brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-0a6cea16e0384785b5094a3c1aa18df6
Source dataset
uspto-grants-1997_01
Patent number
US05594135

Reaction notes

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