HCID 18446528, compound → HCID 18446529, compound

HRID 1268865Notes

Reaction equation

HRID 1268865 reaction equation
[OH:1][CH2:2][C:3]#[C:4][C:5]1[S:6][CH:7]=[CH:8][C:9]=1[CH2:10][CH2:11][C:12]#[N:13]>CO.[Pd]>[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[S:6][CH:7]=[CH:8][C:9]=1[CH2:10][CH2:11][C:12]#[N:13]

Participants

4

Reactant 1

HCID 18446528HCID 18446528, compound

Product 1

HCID 18446529HCID 18446529, compoundYield 66.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 3-[2-(3-hydroxy-prop-1-ynyl)-thiophen-3-yl]-propionitrile 82 (0.27 g, 1.39 mmol) was dissolved in MeOH (5 mL). To this solution was added Pd/C [10% w/w] (0.15 g, 0.14 mmol). The mixture was then stirred under an atmosphere of hydrogen at room temperature for 4 h then filtered through a Celite pad and concentrated in vacuo. Purification by silica gel column chromatography (eluent: 50% EtOAc in hexane) afforded 83 (0.18 g) as a colorless syrup. 1H NMR (400 MHz, d6-DMSO) δ: 7.27 (d, J=5.0 Hz, 1H), 6.94 (d, J=5.0 Hz, 1H), 4.51 (t, J=5.0 Hz 1H), 3.42 (dd, J=6.0 Hz and 11.5 Hz, 2H), 2.82–2.71 (m, 6H), 1.70 (m, 2H). MS (EI) m/z (M+H+) 196, (M−OH+) 178.

Workup

  1. filtrationthen filtered through a Celite pad
  2. concentrationconcentrated in vacuo
  3. customPurification by silica gel column chromatography (eluent: 50% EtOAc in hexane)

Sources & evidence

ORD record
ord-811dadf293de45ba8a0effeefb9eddc1
Source dataset
uspto-grants-2007_04
Patent number
US07199119B2

Reaction notes

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