Bicyclo(2.2.2)oct-5-ene-2,3-dicarboxylic Anhydride → 4-Oxatricyclo[5.2.2.0,2,6]undecane-3,5-dione
Reaction equation
[CH:1]12[CH2:11][CH2:10][CH:7]([CH:8]=[CH:9]1)[CH:6]1[CH:2]2[C:3](=[O:13])[O:4][C:5]1=[O:12]>C(OCC)(=O)C.[Pd]>[CH:7]12[CH2:8][CH2:9][CH:1]([CH2:11][CH2:10]1)[CH:2]1[CH:6]2[C:5](=[O:12])[O:4][C:3]1=[O:13]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
4-Oxa-tricyclo[5.2.2.02,6]undec-8-ene-3,5-dione (4.00 g, 22.45 mmol) was dissolved in ethyl acetate (100 mL). 10% Palladium on carbon (400 mg) was added. The flask was degassed and backfilled with hydrogen gas via balloon. The mixture was stirred at 25° C. for 16 h. The mixture was passed through a plug of Celite and the filtrate was concentrated in vacuo to afford a thick clear oil. Purification by flash column chromatography (Teledyne Isco RediSep column; 0 to 30% ethyl acetate in hexanes) afforded the desired product, 4-oxa-tricyclo[5.2.2.02,6]undecane-3,5-dione (2.92 g, 16.20 mmol, 72%), as a white powder. 1H NMR (400 MHz, DMSO-d6) δ: 1.55-1.64 (6H, m), 1.76 (2H, d, J=9.2 Hz), 2.25 (2H, s), 3.11 (2H, s). LC-MS (ESI) calcd for C10H12O3 180.20, found 181.0 [M+H+].
Workup
- customThe flask was degassed
- concentrationthe filtrate was concentrated in vacuo
- customto afford a thick clear oil
- customPurification by flash column chromatography (Teledyne Isco RediSep column; 0 to 30% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-b6e3eb4abf1b4866b572b7b28f835669
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156832B2
Reaction notes
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