Methanol → Dimethyl 9-(1,3-benzodioxol-5-yl)benzo[g][1,3]benzodioxole-7,8-dicarboxylate

HRID 2354601Notes

Reaction equation

HRID 2354601 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:11]4[C:25](=[O:26])[O:24][C:23](=[O:27])[C:12]=4[CH:13]=[C:14]4[C:22]=3[C:18]3[O:19][CH2:20][O:21][C:17]=3[CH:16]=[CH:15]4)=[CH:9][C:4]=2[O:3][CH2:2]1.[CH3:28][OH:29].[CH3:30][Si](C=[N+]=[N-])(C)C>C1COCC1>[CH3:28][O:29][C:23]([C:12]1[CH:13]=[C:14]2[C:22](=[C:10]([C:8]3[CH:7]=[CH:6][C:5]4[O:1][CH2:2][O:3][C:4]=4[CH:9]=3)[C:11]=1[C:25]([O:24][CH3:30])=[O:26])[C:18]1[O:19][CH2:20][O:21][C:17]=1[CH:16]=[CH:15]2)=[O:27]

Participants

5

Reactant 3

HCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 527377710-Benzo[1,3]dioxol-5-yl-furo[3',4':6,7]naphtho[1,2-d][1,3]dioxole-7,9-dione

Product 1

HCID 5273803Dimethyl 9-(1,3-benzodioxol-5-yl)benzo[g][1,3]benzodioxole-7,8-dicarboxylateYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 1 (108.6 mg, 0.3 mmol) was dissolved to a mixture of MeOH (4 mL) and THF (8 mL). Trimethylsilyldiazomethane (2 M in hexanes, 1.0 mL, 2.0 mmol) was added to the solution. The mixture was stirred for 12 h at room temperature, and then concentrated in vacuo. The residue was purified by chromatography on silica gel using n-hexane/EtOAc (2:1, v/v) to afford 30 (67 mg, 55%) as a pale yellow powder. mp 157-159° C.; 1H NMR (CDCl3) δ 8.53 (s, 1H, H4), 7.58 (d, 1H, H5, J=8.7 Hz), 7.27 (d, 1H, H6, J=8.7 Hz), 6.79-6.82 (m, 3H, H2′+H5′+H6′), 6.03 (AB, 2H, 3′,4′-OCH2O—, Δδ=10.2 Hz, J=1.5 Hz), 5.89 (AB, 2H, 7,8-OCH2O—, Δδ=7.2 Hz, J=1.5 Hz), 3.94, 3.66 (each s, 2×3H, 2×OCH3); MS (EI) m/z 408 [M]+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-dd0a538764f84477864dd48f5369455c
Source dataset
uspto-grants-2010_07
Patent number
US07754718B2

Reaction notes

Loading…