1-Methoxybicyclo[2.2.2]oct-5-en-2-one → 1-Methoxybicyclo[2.2.2]octan-2-one

HRID 451792Notes

Reaction equation

HRID 451792 reaction equation
[CH3:1][O:2][C:3]12[CH2:10][CH2:9][CH:6]([CH:7]=[CH:8]1)[CH2:5][C:4]2=[O:11]>CO.[Ni]>[CH3:1][O:2][C:3]12[CH2:8][CH2:7][CH:6]([CH2:9][CH2:10]1)[CH2:5][C:4]2=[O:11]

Participants

4

Reactant 1

HCID 3772231-Methoxybicyclo[2.2.2]oct-5-en-2-one

Product 1

HCID 217686131-Methoxybicyclo[2.2.2]octan-2-oneYield 90%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 1-methoxybicyclo[2.2.2]oct-5-en-2-one (16.5 g, 0.11 mol) in MeOH (250 mL) was added Raney-Ni (3.3 g). The reaction mixture was stirred at 40° C. and 45 psi under H2 atmosphere for 2-3 h (8.0 g, 40%). The resulting mixture was filtered, the filtrate was concentrated in vacuo to produce 1-methoxybicyclo[2.2.2]octan-2-one (15.0 g, 90%). 1H NMR (CDCl3, 400 MHz) δ 3.33 (s, 3H), 2.32 (d, 2H), 2.09 (m, 1H), 1.49-1.95 (m, 8H).

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-334818d8860942d78f279165d2eb22f8
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

Loading…