Triethylsilane → HCID 18545868, compound

HRID 1385069Notes

Reaction equation

HRID 1385069 reaction equation
[CH3:1][C:2]1[C:7]2[CH:8]([C:12]([OH:14])=[O:13])[CH2:9][C:10](=O)[C:6]=2[CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:7]=1[CH:8]([C:12]([OH:14])=[O:13])[CH2:9][CH2:10]2

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 2895327-Methyl-3-oxo-2,3-dihydro-1H-indene-1-carboxylic acid

Product 1

HCID 18545868HCID 18545868, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 12a (100 g) in trifluoroacetic acid is added trietylsilane (141 g). The mixture was stirred for 72 hours at room temperature and was then evaporated in vacuo the residue was dissolved in ethyl acetate and was extracted with dilute NaOH solution. The aqueous phase was washed with ethyl acetate and was then acidified with concentrated hydrochloric acid. Conventional work up with ethyl acetate gave 80.4 g of crude product. Purification on silica gel eluted with ethyl acetate-heptane-acetic acid gave the title compound (76.6 g).

Workup

  1. customwas then evaporated in vacuo the residue
  2. dissolutionwas dissolved in ethyl acetate
  3. extractionwas extracted with dilute NaOH solution
  4. washThe aqueous phase was washed with ethyl acetate
  5. customgave 80.4 g of crude product
  6. customPurification on silica gel
  7. washeluted with ethyl acetate-heptane-acetic acid

Sources & evidence

ORD record
ord-5ab4e72572de4ff4b04e6feb9d210e9a
Source dataset
uspto-grants-2001_07
Patent number
US06262087B1

Reaction notes

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