Diethyl 9-(1,3-benzodioxol-5-yl)-6-hydroxy-benzo[g][1,3]benzodioxole-7,8-dicarboxylate → 10-Benzo[1,3]dioxol-5-yl-6-hydroxy-7H-furo[3',4':6,7]naphtho[1,2-d][1,3]dioxol-9-one

HRID 2354604Notes

Reaction equation

HRID 2354604 reaction equation
C(O[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]CC)=[O:20])[C:12]1[O:13][CH2:14][O:15][C:11]=1[CH:10]=[CH:9]2)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[O:28]1[C:27]2[CH:31]=[CH:32][C:24]([C:17]3[C:18]4[C:19](=[O:21])[O:20][CH2:4][C:6]=4[C:7]([OH:33])=[C:8]4[C:16]=3[C:12]3[O:13][CH2:14][O:15][C:11]=3[CH:10]=[CH:9]4)=[CH:25][C:26]=2[O:30][CH2:29]1

Participants

4

Reactant 2

HCID 5273806Diethyl 9-(1,3-benzodioxol-5-yl)-6-hydroxy-benzo[g][1,3]benzodioxole-7,8-dicarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 527380710-Benzo[1,3]dioxol-5-yl-6-hydroxy-7H-furo[3',4':6,7]naphtho[1,2-d][1,3]dioxol-9-oneYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 33 (45.2 mg, 0.1 mmol) in THF (1 mL) was added dropwise to a suspension of lithium aluminum hydride (7.6 mg, 0.2 mmol) in THF (1 mL) at 0° C. The mixture was stirred at room temperature for 2 h and quenched with aqueous saturated Na2SO4 solution, and then extracted with CHCl3 (2×30 mL). After evaporation of organic solvent, the residue was purified by column chromatography on silica gel using CH2Cl2/MeOH (20:1, v/v) to give 34 (36 mg, 99%) as a yellow powder. mp 257° C. (decomp.); 1H NMR (DMSO-d6) δ 10.67 (s, 1H, 4OH), 7.94 (d, 1H, H5, J=9.0 Hz), 7.44 (d, 1H, H6, J=9.0 Hz), 6.84 (d, 1H, H5′, J=8.1 Hz), 6.79 (d, 1H, H2′, J=1.5 Hz), 6.66 (dd, 1H, H6′, J=1.5, 8.1 Hz), 6.04 (AB, 2H, 3′,4′-OCH2O—, Δδ=6.0 Hz, J=0.6 Hz), 5.88 (AB, 2H, 7,8-OCH2O—, Δδ=6.3 Hz, J=0.9 Hz), 5.32 (s, 2H, lactone-CH2—); MS (FAB, positive) m/z 365 [M+H]+.

Workup

  1. customquenched with aqueous saturated Na2SO4 solution
  2. extractionextracted with CHCl3 (2×30 mL)
  3. customAfter evaporation of organic solvent
  4. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-05b15df785cf41a4b395a2fe5c9634aa
Source dataset
uspto-grants-2010_07
Patent number
US07754718B2

Reaction notes

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