3,4-Bis-(1,1-dimethyl-allyloxy)-xanthen-9-one → 17,17-Dimethyl-15-(3-methylbut-2-enyl)-3,16-dioxapentacyclo[11.4.1.02,11.02,15.04,9]octadeca-4,6,8,11-tetraene-10,14-dione

HRID 734186Notes

Reaction equation

HRID 734186 reaction equation
CC(C)([O:5][C:6]1[CH:7]=[CH:8][C:9]2[C:10](=[O:26])[C:11]3[C:16]([O:17][C:18]=2[C:19]=1[O:20][C:21]([CH3:25])([CH3:24])[CH:22]=[CH2:23])=[CH:15][CH:14]=[CH:13][CH:12]=3)C=C>C1(C)C=CC=CC=1>[CH3:18][C:9]([CH3:10])=[CH:8][CH2:7][C:19]12[C:6](=[O:5])[CH:7]3[CH:8]=[C:9]4[C:18]1([CH:22]([CH2:23]3)[C:21]([CH3:25])([CH3:24])[O:20]2)[O:17][C:16]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:10]4=[O:26]

Participants

3

Reactant 1

HCID 161050363,4-Bis-(1,1-dimethyl-allyloxy)-xanthen-9-one

Product 1

HCID 1131451817,17-Dimethyl-15-(3-methylbut-2-enyl)-3,16-dioxapentacyclo[11.4.1.02,11.02,15.04,9]octadeca-4,6,8,11-tetraene-10,14-dioneYield 135.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3,4-bis-(1,1-dimethyl-allyloxy)-xanthen-9-one (229 mg, 0.587 mmol) in toluene (10 mL) was refluxed under argon for 2 h. The solvent was evaporated and the residue was purified by column chromatography (SiO2, EtOAc:hexanes/10-30%) to give the title compound as white solids (145 mg, 63%): 1H NMR (CDCl3, 300 MHz) δ 7.95 (dd, J=1.5, 7.8 Hz, 1H), 7.53 (ddd, J=1.5, 7.2, 8.1 Hz, 1H), 7.44 (dd, J=0.6, 7.2 Hz, 1H), 7.07 (m, 2H), 4.42 (m, 1H), 3.50 (dd, J=4.5, 6.9 Hz, 1H), 2.63 (m, 2H), 2.46 (d, J=9.3 Hz, 1H), 2.35 (dd, J=4.2, 12.6 Hz, 1H), 1.73 (s, 3H), 1.31 (m, 1H), 1.31 (s, 6H), 0.92 (s, 3H); 13C NMR (CDCl3, 75 MHz) δ 202.8, 176.3, 159.5, 136.1, 134.8, 134.7, 133.6, 126.8, 121.8, 119.0, 118.9, 118.0, 90.3, 84.6, 83.5, 48.8, 46.8, 30.4, 29.2, 25.4, 25.2, 16.8.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by column chromatography (SiO2, EtOAc:hexanes/10-30%)

Sources & evidence

ORD record
ord-f9732913ebfe45d79b8d50ccf30a79c8
Source dataset
uspto-grants-2009_09
Patent number
US07592143B2

Reaction notes

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