Triethylsilane → HCID 18545868, compound

HRID 275710Notes

Reaction equation

HRID 275710 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 etyl 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 etyl 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-3086b06997da4e0799f585676bc84d58
Source dataset
uspto-grants-2002_03
Patent number
US06352988B2

Reaction notes

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