2-(17-(4-Nitrophenoxy)-3,6,9,12,15-pentaoxaheptadecyloxy)tetrahydro-2H-pyran → 4-(17-(Tetrahydro-2H-pyran-2-yloxy)-3,6,9,12,15-pentaoxaheptadecyloxy)aniline

HRID 78714Notes

Reaction equation

HRID 78714 reaction equation
[N+:1]([C:4]1[CH:34]=[CH:33][C:7]([O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)=[CH:6][CH:5]=1)([O-])=O>[Pd]>[O:28]1[CH2:29][CH2:30][CH2:31][CH2:32][CH:27]1[O:26][CH2:25][CH2:24][O:23][CH2:22][CH2:21][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][O:8][C:7]1[CH:33]=[CH:34][C:4]([NH2:1])=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 867098922-(17-(4-Nitrophenoxy)-3,6,9,12,15-pentaoxaheptadecyloxy)tetrahydro-2H-pyran

Product 1

HCID 867098934-(17-(Tetrahydro-2H-pyran-2-yloxy)-3,6,9,12,15-pentaoxaheptadecyloxy)anilineYield 98.3%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a stirred solution of 35 (6.30 g, 12.9 mmol) in 1:1 THF/TEA (26 mL) in a Parr apparatus was added a catalytic amount of 20% Pd/C (0.05 g). The reaction vessel was purged with hydrogen then pressurized to 70 psi. After stirring for 16 h the reaction mixture was filtered through a 4 cm pad of celite and concentrated under reduced pressure to afford 36 as a brown oil (5.80 g, 98%): 1H NMR (300 MHz, CDCl3) δ 6.75 (d, J=8.9 Hz, 2H), 6.62 (d, J=8.9 Hz, 2H), 4.71-4.55 (m, 1H), 4.09-4.00 (m, 2H), 3.94-3.31 (m, 22H), 1.93-1.44 (m, 6H).

Workup

  1. customThe reaction vessel was purged with hydrogen
  2. filtrationwas filtered through a 4 cm pad of celite
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4985d9f9be7d4727be9c5f1226f13825
Source dataset
uspto-grants-2014_09
Patent number
US08841460B2

Reaction notes

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