Ethanol → HCID 86592154, compound

HRID 1374883Notes

Reaction equation

HRID 1374883 reaction equation
C(O[CH2:9][C@@H:10]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:11]([OH:13])=[O:12])C1C=CC=CC=1.CC[OH:21]>[Pd]>[OH:21][CH:16]([CH2:17][CH3:18])[CH2:15][CH2:14][C@@H:10]([CH3:9])[C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 702EthanolHCID 66603396HCID 66603396, compound

Product 1

HCID 86592154HCID 86592154, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of (R)-3-benzyloxy-2-pentyl-propionic acid (1.54 g, 6.16 mmol) in EtOH (100 mL) was added 10% Pd/C (310 mg). The reaction mixture was subjected to hydrogenation overnight at room temperature. After the reaction was completed, the reaction mixture was filtered through a pad of Celite, and washed with EtOH (50 mL×3). Removal of the solvent provided the title compound (0.92 g, 93%). No further purification was required. 1H NMR (400 MHz, CHCl3) δ 6.30 (br s, 1H), 3.81 (d, J=5.4 Hz, 2H), 2.64 (m, 1H), 1.69 (m, 1H), 1.56 (m, 1H), 1.41–1.27 (m, 6H), 0.91 (t, J=7.7 Hz, 3H). Mass spectrum ES+: 161 [M+H]+.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of Celite
  2. washwashed with EtOH (50 mL×3)
  3. customRemoval of the solvent

Sources & evidence

ORD record
ord-cd20d608302344e084e4a4b0922ea5e5
Source dataset
uspto-grants-2007_01
Patent number
US07166624B2

Reaction notes

Loading…