HCID 58703563, compound → HCID 68527018, compound

HRID 1179468Notes

Reaction equation

HRID 1179468 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH2:9][CH2:8][CH2:7][C:6]=1[C:10]1[CH:15]=[C:14]([O:16][CH2:17][O:18][CH3:19])[CH:13]=[C:12]([CH2:20][O:21][CH3:22])[C:11]=1[O:23][CH2:24][O:25][CH3:26])=[O:4]>CCO>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH2:7][CH:6]1[C:10]1[CH:15]=[C:14]([O:16][CH2:17][O:18][CH3:19])[CH:13]=[C:12]([CH2:20][O:21][CH3:22])[C:11]=1[O:23][CH2:24][O:25][CH3:26])=[O:4]

Participants

3

Reactant 1

HCID 58703563HCID 58703563, compound

Product 1

HCID 68527018HCID 68527018, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Stir a solution of 2-(2,5-bis-methoxymethoxy-3-methoxymethyl-phenyl)-cyclopent-1-enecarboxylic acid methyl ester (1.76 g, 4.80 mmol) in EtOH (75 mL, pre-filtered through a plug of basic alumina) for 1 minute with activated carbon, then filter through Celite®. Add 10% Pd/C (50% wet, 0.83 g) to the filtrate and hydrogenate this mixture at 55-60 psi for at least 20 hours. Filter the reaction through Celite® and concentrate the filtrate to afford the subtitled product (1.20 g, 68%) as an oil that may be used without further purification. 1H NMR (CDCl3) δ 1.63-1.74 (m, 1H), 1.92-2.10 (m, 4H), 2.11-2.20 (m, 1H), 3.20-3.27 (m, 4H), 3.40 (s, 3H), 3.46 (s, 3H), 3.60 (s, 3H), 3.69-3.78 (m, 1H), 4.44-1.53 (m, 2H), 4.95-5.01 (m, 2H), 5.08-5.14 (m, 2H), 6.80 (d, J=3.0 Hz, 1H), 6.94 (d, J=3.0 Hz, 1H).

Workup

  1. filtrationpre-filtered through a plug of basic alumina) for 1 minute with activated carbon
  2. filtrationfilter through Celite®
  3. additionAdd 10% Pd/C (50% wet, 0.83 g) to the filtrate and hydrogenate this mixture at 55-60 psi for at least 20 hours
  4. filtrationFilter
  5. customthe reaction through Celite®
  6. concentrationconcentrate the filtrate

Sources & evidence

ORD record
ord-9f873da388964860bfd5efb3fc502dca
Source dataset
uspto-grants-2007_10
Patent number
US07279499B2

Reaction notes

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