tert-Butyl 3-(2-(2-(benzyloxy)ethoxy)ethoxy)-2,2-dimethylpropanoate → tert-Butyl 3-(2-(2-hydroxyethoxy)ethoxy)-2,2-dimethylpropanoate

HRID 1507748Notes

Reaction equation

HRID 1507748 reaction equation
C([O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][C:16]([CH3:25])([CH3:24])[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])C1C=CC=CC=1>CCO.[Pd]>[OH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][C:16]([CH3:25])([CH3:24])[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]

Participants

4

Reactant 1

HCID 117642942tert-Butyl 3-(2-(2-(benzyloxy)ethoxy)ethoxy)-2,2-dimethylpropanoate

Product 1

HCID 117642669tert-Butyl 3-(2-(2-hydroxyethoxy)ethoxy)-2,2-dimethylpropanoateYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of tert-butyl 3-(2-(2-(benzyloxy)ethoxy)ethoxy)-2,2-dimethylpropanoate (48) (13 g, 37 mmol) and 10% Pd/C (1.3 g) in EtOH (92 mL) were placed under 5 bar of H2 pressure (isolated system), and stirred for 16 h. The mixture was filtered through celite and the filtrate concentrated in vacuo to afford tert-butyl 3-(2-(2-hydroxyethoxy)ethoxy)-2,2-dimethylpropanoate (49) (8.2 g, 85%) as a colourless oil: m/z 285 (M+Na)+ (ES+). 1H NMR (400 MHz, CDCl3) δ: 3.73-3.69 (m, 2H), 3.66-3.58 (m, 6H), 3.44 (s, 2H), 2.37 (t, J=6.2 Hz, 1H), 1.43 (s, 9H), 1.14 (s, 6H).

Workup

  1. customwere placed under 5 bar of H2 pressure (isolated system)
  2. filtrationThe mixture was filtered through celite
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-1183d19bb3c04e809b95441b19947fe0
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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