Ethyl Acetate → HCID 19906362, compound

HRID 2371808Notes

Reaction equation

HRID 2371808 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([NH:5][C:6]1[CH:14]=[C:13]2[C:9]([CH2:10][CH2:11][C:12]2=[O:15])=[CH:8][CH:7]=1)=[O:4].C(OCC)(=O)C>[Pd].CN(C)C=O>[OH:15][CH:12]1[C:13]2[C:9](=[CH:8][CH:7]=[C:6]([NH:5][C:3](=[O:4])[C:2]([F:16])([F:17])[F:1])[CH:14]=2)[CH2:10][CH2:11]1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 19906408HCID 19906408, compound

Product 1

HCID 19906362HCID 19906362, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 10% (w/w) palladium on carbon (2.34 g), 6-(trifluoroacetamido)indan-1-one (7.79 g), ethyl acetate (53 ml) and dimethylformamide (11 ml) was hydrogenated at atmospheric pressure for 72 h. The reaction mixture was filtered through diatomaceous earth with ethyl acetate wash and evaporated. The residue was flash chromatographed, eluting with 95:5 methylene chloride:methanol, and triturated with ether to give 1-hydroxy-6-(trifluoroacetamido)indane (4.41 g, 56%) as a colorless solid; mp 123.0°-124.5° C.; MS(EI), m/e=245(M+.).

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth with ethyl acetate
  2. washwash
  3. customevaporated
  4. customchromatographed
  5. washeluting with 95:5 methylene chloride
  6. custommethanol, and triturated with ether

Sources & evidence

ORD record
ord-28712b2f986e4d909e9c82d8aab31a17
Source dataset
uspto-grants-1992_03
Patent number
US05095038

Reaction notes

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