Reaction equation
[CH3:1][O:2][C:3]1[C:16]2[C:7](=[CH:8][C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:6]([O:17][CH3:18])=[CH:5][CH:4]=1.[CH3:19][O:20][C:21]1[CH:27]=[C:26]([OH:28])[CH:25]=[CH:24][C:22]=1[OH:23]>C1(C)C=CC=CC=1>[CH3:18][O:17][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:16]2[C:7]=1[CH:8]1[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:15]2[CH:24]2[C:22]([C:21]([O:20][CH3:19])=[CH:27][C:26](=[O:28])[CH:25]12)=[O:23]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A solution of 0.70 g (2.90 mmol) of 2 and 1.00 g (7.20 mmol) of 6 in 10 mL of toluene in a sealed tube was heated at 150° C. for 1 day, cooled to 25° C., concentrated to dryness, and column chromatographed on silica gel using a gradient mixture of hexane and ethyl acetate as solvent gave 0.52 g (48% yield) of compounds 5 as a mixture of exo- and endo-(1:1) isomers along with 0.62 g of 6. The exo- and endo-isomers were partially separated by silica gel column and the stereochemistry have not assigned. Compound 5, less polar isomer: MS, m/z 376 (M+), 375. 1H NMR d 7.24-7.18 (m, 2H), 7.08-7.04 (m, 2H), 6.65 (s, 2H, C6,7 Hs), 5.61 (s, 1H), 5.33 (bs, 2H), 3.82 (s, 6H, OMe), 3.48 (s, 3H, OMe), 3.12 (ABd, J=9 Hz, 1H), 3.06 (ABd, J=9 Hz, 1H). More polar isomer: MS, m/z 376 (M+), 375. 1H NMR d 7.40 (m, 2H), 7.16 (m, 2H), 6.60 (ABd, J=8.8 Hz, 1H), 6.56 (Abd, J=8.8 Hz, 1H), 5.65 (s, 1H, ═CH), 5.33 (bs, 2H, C9,10 Hs), 3.76 (s, 3H, OMe), 3.73 (s, 3H, OMe), 3.51 (s, 3H, OMe), 3.13 (Abd, J=9 Hz, 1H), 3.08 (Abd, J=9 Hz, 1H). This mixture of compounds was used in the next step.
Workup
- concentrationconcentrated to dryness, and column
- customchromatographed on silica gel using
- additiona gradient mixture of hexane and ethyl acetate as solvent
Sources & evidence
- ORD record
- ord-5e45cc1ea98e4902b7704c132fe8fe70
- Source dataset
- uspto-grants-2004_12
- Patent number
- US06828450B2
Linked notes
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