HCID 68696410, compound → HCID 17993212, compound

HRID 1990981Notes

Reaction equation

HRID 1990981 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5](/[CH:10]=[CH:11]/[CH2:12][OH:13])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1>[Pd].C(O)C.C(OCC)(=O)C>[NH:1]1[C:9]2[C:4](=[C:5](/[CH:10]=[CH:11]/[CH2:12][OH:13])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[NH:1]1[C:9]2[C:4](=[C:5]([CH2:10][CH2:11][CH2:12][OH:13])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

6

Reactant 1

HCID 68696410HCID 68696410, compound

Product 2

HCID 17993212HCID 17993212, compoundYield 185.5%HCID 68696410HCID 68696410, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 10% palladium on carbon (200 mg) in absolute ethanol (30 mL) was added a solution of (2E)-3-(1H-indol-4-yl)prop-2-en-1-ol (0.98 g, 5.66 mmol) in ethyl acetate (30 mL) and the mixture hydrogenated at 50 psi for 15 min. The reaction mixture was filtered through celite and concentrated in vacuo to give a light purple syrup. (2E)-3-(1H-indol-4-yl)prop-2-en-1-ol was prepared by the method of Kardos, N.; Genet J-P. Tetrahedron Asymmetry 1994, 5, 1525-1533, which is incorporated herein by reference in its entirety. Purification by flash chromatography (20% to 50% ethyl acetate/hexane) gave the title compound as a colorless syrup (0.92 g, 93%). MS (ES+) m/z 176.2 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered through celite and
  2. concentrationconcentrated in vacuo
  3. customto give a light purple syrup
  4. customPurification by flash chromatography (20% to 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-dff3d954f9724f918526dca278fbf08e
Source dataset
uspto-grants-2010_01
Patent number
US07645752B2

Reaction notes

Loading…