Methyl 2-[3-(2-tert-butylsilyloxypropan-2-yl)-2,5-bis(methoxymethoxy)phenyl]cyclopentene-1-carboxylate → Methyl 2-[3-(2-tert-butylsilyloxypropan-2-yl)-2,5-bis(methoxymethoxy)phenyl]cyclopentane-1-carboxylate

HRID 1179470Notes

Reaction equation

HRID 1179470 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]([C:20]([CH3:28])([CH3:27])[O:21][SiH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:11]=1[O:29][CH2:30][O:31][CH3:32])=[O:4]>CCO.[Pd]>[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]([C:20]([CH3:27])([CH3:28])[O:21][SiH2:22][C:23]([CH3:25])([CH3:26])[CH3:24])[C:11]=1[O:29][CH2:30][O:31][CH3:32])=[O:4]

Participants

4

Reactant 1

HCID 131726630Methyl 2-[3-(2-tert-butylsilyloxypropan-2-yl)-2,5-bis(methoxymethoxy)phenyl]cyclopentene-1-carboxylate

Product 1

HCID 131726629Methyl 2-[3-(2-tert-butylsilyloxypropan-2-yl)-2,5-bis(methoxymethoxy)phenyl]cyclopentane-1-carboxylateYield 84.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Filter a solution of 2-[3-(tert-butyl-dimethyl-silanyloxymethyl)-2,5-bis-methoxymethoxy-phenyl]-cyclopent-1-enecarboxylic acid methyl ester (0.715 g, 1.53 mmol) in EtOH (40 mL) through a 1×6 cm pad of activated carbon. Add the filtrate to a Pair® bottle containing 10% Pd/C (50% wet, 0.15 g) and hydrogenate this mixture at 55-60 psi for 3 hours. Filter the reaction through Celite® and concentrate the filtrate to afford the subtitled product (0.605 g, 84%) as an oil that may be used without further purification. 1H NMR (CDCl3) δ 0.10 (s, 3H), 0.11 (s, 3H), 0.94 (s, 9H), 1.60-1.67 (m, 1H), 1.91-2.04 (m, 4H), 2.11-2.18 (m, 1H), 3.22 (s, 3H), 3.17-3.24 (m, 1H), 3.45 (s, 3H), 3.58 (s, 3H), 3.65-3.72 (m, 1H), 4.79 (s, 2H), 4.95 (dd, J=5.8, 6.8 Hz, 2H), 5.10 (dd, J=6.6, 9.6 Hz, 2H), 6.74 (d, J=3.0 Hz, 1H), 7.04 (d, J=3.0 Hz, 1H).

Workup

  1. additionAdd the filtrate to a Pair® bottle
  2. filtrationFilter
  3. customthe reaction through Celite®
  4. concentrationconcentrate the filtrate

Sources & evidence

ORD record
ord-fdb5966882e34480844a76816a54ef66
Source dataset
uspto-grants-2007_10
Patent number
US07279499B2

Reaction notes

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