HCID 118184930, compound → HCID 118184912, compound

HRID 2177402Notes

Reaction equation

HRID 2177402 reaction equation
[F:1][C:2]1([F:20])[C:10]2[C:5](=[C:6]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:7]=[C:8](I)[C:9]=2[OH:11])[CH2:4][CH2:3]1.[H][H]>[Pd].C(OCC)(=O)C>[F:1][C:2]1([F:20])[C:10]2[C:5](=[C:6]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:7]=[CH:8][C:9]=2[OH:11])[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 118184930HCID 118184930, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 118184912HCID 118184912, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

Into a 50-mL round-bottom flask was placed ethyl 3-(1,1-difluoro-7-hydroxy-6-iodo-2,3-dihydro-1H-inden-4-yl)propanoate (80 mg, 0.20 mmol, 1.00 equiv), ethyl acetate (3 mL), Palladium on carbon (80 mg) and hydrogen was introduced last. The resulting solution was stirred overnight at 25° C. The solids were removed by filtration and the filtrate was concentrated under reduced pressure. The resultant residue was purified by TLC with ethyl acetate/petroleum ether (1:3) to give 40 mg (73%) of ethyl 3-(1,1-difluoro-7-hydroxy-2,3-dihydro-1H-inden-4-yl)propanoate as a colorless oil. Mass spectrum (ESI, m/z): Calcd. for C14H16F2O3, 269.1 (M−H). found 269.1.

Workup

  1. customInto a 50-mL round-bottom flask was placed
  2. customThe solids were removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resultant residue was purified by TLC with ethyl acetate/petroleum ether (1:3)

Sources & evidence

ORD record
ord-2fb7a6b111d744838b1a7965da57bc43
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

Loading…