Trimethylsilyldiazomethane → Diethyl 9-(1,3-benzodioxol-5-yl)-6-methoxy-benzo[g][1,3]benzodioxole-7,8-dicarboxylate

HRID 2354605Notes

Reaction equation

HRID 2354605 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:33])=[C:8]2[C:16](=[C:17]([C:24]3[CH:32]=[CH:31][C:27]4[O:28][CH2:29][O:30][C:26]=4[CH:25]=3)[C:18]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:12]1[O:13][CH2:14][O:15][C:11]=1[CH:10]=[CH:9]2)=[O:5])[CH3:2].[CH3:34][Si](C=[N+]=[N-])(C)C>CO.C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:33][CH3:34])=[C:8]2[C:16](=[C:17]([C:24]3[CH:32]=[CH:31][C:27]4[O:28][CH2:29][O:30][C:26]=4[CH:25]=3)[C:18]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:12]1[O:13][CH2:14][O:15][C:11]=1[CH:10]=[CH:9]2)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 5273806Diethyl 9-(1,3-benzodioxol-5-yl)-6-hydroxy-benzo[g][1,3]benzodioxole-7,8-dicarboxylate

Product 1

HCID 5273808Diethyl 9-(1,3-benzodioxol-5-yl)-6-methoxy-benzo[g][1,3]benzodioxole-7,8-dicarboxylateYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 33 (95 mg, 0.21 mmol) was dissolved in a mixture of MeOH (3 mL) and THF (6 mL). (Trimethylsilyl)diazomethane (2 M in hexanes, 0.6 mL, 1.2 mmol) was added to the solution. The mixture was stirred for 12 h at room temperature, and then concentrated in vacuo. The crude material was purified by column chromatography on silica gel using CH2Cl2 to afford 35 (97 mg, 99%) as a yellow oil. 1H NMR (CDCl3) δ 7.86 (d, 1H, H5, J=8.7 Hz), 7.26 (d, 1H, H6, J=8.7 Hz), 6.75-6.82 (m, 3H, H2′+H5′+H6′), 6.00 (AB, 2H, 3′,4′-OCH2O—, Δδ=11.7 Hz, J=1.2 Hz), 5.87 (AB, 2H, 7,8-OCH2O—, Δδ=9.0 Hz, J=1.2 Hz), 4.39 (q, 2H, OCH2CH3, J=7.2 Hz), 4.06 (s, 3H, 4-OCH3), 4.03 (q, 2H, OCH2CH3, J=7.2 Hz), 1.38, 1.04 (each t, 2×3H, 2×OCH2CH3, J=7.2 Hz); MS (EI) m/z 466 [M]+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude material was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d20c0201716b4f00b84989b89e5b3c7d
Source dataset
uspto-grants-2010_07
Patent number
US07754718B2

Reaction notes

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