6-{2-[2-(2-{2-[2-(2-Benzyloxyethoxy)ethoxy]ethoxy}-ethoxy)-ethoxy]-ethoxy}-hexanoic acid ethyl ester → 6-{2-[2-(2-{2-[2-(2-Hydroxyethoxy)ethoxy]ethoxy}-ethoxy)ethoxy]-ethoxy}-hexanoic acid ethyl ester

HRID 983778Notes

Reaction equation

HRID 983778 reaction equation
[CH2:1]([O:3][C:4](=[O:36])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28]CC1C=CC=CC=1)[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:36])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][OH:28])[CH3:2]

Participants

4

Reactant 1

HCID 687199766-{2-[2-(2-{2-[2-(2-Benzyloxyethoxy)ethoxy]ethoxy}-ethoxy)-ethoxy]-ethoxy}-hexanoic acid ethyl ester

Product 1

HCID 865870286-{2-[2-(2-{2-[2-(2-Hydroxyethoxy)ethoxy]ethoxy}-ethoxy)ethoxy]-ethoxy}-hexanoic acid ethyl esterYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Substantially monodispersed benzyl ether 3 (1.03 g, 2.0 mmol) was dissolved in 25 ml ethanol. To this solution was added 270 mg 10% Pd/C, and the mixture was placed under a hydrogen atmosphere and stirred for four hours, at which time TLC showed the complete disappearance of the starting material. The reaction mixture was filtered through Celite 545 to remove the catalyst, and the filtrate was concentrated in vacuo to yield the monodispersed compound 4 as a clear oil (0.67 g, 79%). FAB MS: m/e 425 (M+H), 447 (M+Na).

Workup

  1. filtrationThe reaction mixture was filtered through Celite 545
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-5026f8b49e184c64bea4cf7b373e749d
Source dataset
uspto-grants-2005_03
Patent number
US06867183B2

Reaction notes

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