Epichlorohydrin → 1,3-bis(oxiran-2-ylmethoxy)-12H-benzo[b]xanthen-12-one

HRID 83110

Reaction equation

[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[CH:12]=[C:11]4[CH:17]=[CH:18][CH:19]=[CH:20][C:10]4=[CH:9][C:8]=3[O:7][C:6]=2[CH:5]=[C:4]([OH:21])[CH:3]=1.[CH2:22]([CH:24]1[O:26][CH2:25]1)Cl>CC(C)=O>[O:26]1[CH2:25][CH:24]1[CH2:22][O:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[CH:12]=[C:11]4[CH:17]=[CH:18][CH:19]=[CH:20][C:10]4=[CH:9][C:8]=3[O:7][C:6]=2[CH:5]=[C:4]([O:21][CH2:22][CH:24]2[CH2:25][O:26]2)[CH:3]=1

Participants

Conditions

Temperature: 57.5 °C

Procedure

1,3-dihydroxy-12H-benzo[b]xanthen-12-one (0.15 g, 0.54 mmol) synthesized in Step 1 of Example 18, CS2CO3 (0.53 g, 1.62 mmol), and anhydrous acetone (30 mL) were charged to a dry round-bottom flask, and epichlorohydrin (0.25 g, 2.7 mmol) was added thereto with stirring using a syringe. The reaction mixture was stirred with reflux under a nitrogen atmosphere (55 to 60° C., overnight). Solid of the reaction mixture was filtered and removed, and the filtrate was concentrated under reduced pressure. The resulting residue was separated and purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:3 (v/v)) to give the title compound (15.3 mg, 21.8%) as a yellow solid.

Workup

stirringThe reaction mixture was stirred
filtrationSolid of the reaction mixture was filtered
customremoved
concentrationthe filtrate was concentrated under reduced pressure
customThe resulting residue was separated
custompurified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:3 (v/v))

Sources & evidence

ORD record: ord-1d03c9ea32d24eaebcef6e626a5f8f1c
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846749B2

Linked notes

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