Sodium Hydroxide → HCID 23692353, compound

HRID 2354609Notes

Reaction equation

HRID 2354609 reaction equation
[OH-:1].[Na+:2].[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]3[C:13]4[CH2:28][O:27][C:26](=[O:29])[C:14]=4[CH:15]=[C:16]4[C:24]=3[C:20]3[O:21][CH2:22][O:23][C:19]=3[CH:18]=[C:17]4[Cl:25])=[CH:11][C:6]=2[O:5][CH2:4]1>CO>[Na+:2].[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]3[C:13]([CH2:28][OH:1])=[C:14]([C:26]([O-:27])=[O:29])[CH:15]=[C:16]4[C:24]=3[C:20]3[O:21][CH2:22][O:23][C:19]=3[CH:18]=[C:17]4[Cl:25])=[CH:11][C:6]=2[O:5][CH2:4]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 527381010-Benzo[1,3]dioxol-5-yl-5-chloro-9H-furo[3',4':6,7]naphtho[1,2-d][1,3]dioxol-7-one

Product 1

HCID 23692353HCID 23692353, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

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]+.

Workup

  1. customThe solvent was evaporated
  2. customto give a crude product, which
  3. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4225957c81094196894362c6bddfe6ce
Source dataset
uspto-grants-2010_07
Patent number
US07754718B2

Reaction notes

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