Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 10-Benzo[1,3]dioxol-5-yl-5-chloro-9H-furo[3',4':6,7]naphtho[1,2-d][1,3]dioxol-7-one | HCID 5273810 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 23692353 | HCID 23692353 | 87% |
Reaction Steps
1 N aqueous NaOH solution (1.56 mL) was added to the solution of 37 (57 mg, 0.15 mmol) in MeOH (25 mL). The mixture was stirred at 70° C. for 1 h. The solvent was evaporated to give a crude product, which was purified by silica gel column chromatography using CH2Cl2/MeOH (3:1, v/v) to afford 44 (55 mg, 87%) as a white powder. mp 220° C. (decomp.); 1H NMR (DMSO-d6) δ 8.39 (s, 1H, H4), 7.54 (s, 1H, H6), 6.89 (d, 1H, H5′, J=8.7 Hz), 6.73 (d, 1H, H2′, J=1.5 Hz), 6.63 (dd, 1H, H6′, J=1.5, 8.7 Hz), 6.05 (AB, 2H, 3′,4′-OCH2O—, Δδ=18.9 Hz), 5.81 (AB, 2H, 7,8-OCH2O—, A5=8.1 Hz), 4.12 (s, 2H, 2-CH2OH); MS (FAB, positive) m/z 425 [M+H+2]+, 423 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07754718B2 |
|---|
| Source dataset | uspto-grants-2010_07 |
|---|
| ORD ID | ord-4225957c81094196894362c6bddfe6ce |
|---|
| Source note | uspto-grants-2010_07 |
|---|
