Acetone → 8-(Benzyloxy)-5-[(2S)oxiranylmethoxy]-3,4-dihydro-2(1H)-quinolinone

HRID 1281481Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:13])[NH:7]2.C(=O)([O-])[O-].[K+].[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH3:28][C:29]([CH3:31])=[O:30]>>[CH2:20]([O:12][C:9]1[CH:10]=[CH:11][C:2]([O:1][CH2:28][C@@H:29]2[CH2:31][O:30]2)=[C:3]2[C:8]=1[NH:7][C:6](=[O:13])[CH2:5][CH2:4]2)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Reactant 4

HCID 180Acetone

HCID 7498Benzyl Bromide

HCID 11430Potassium Carbonate

HCID 1515652(1H)-Quinolinone, 3,4-dihydro-5,8-dihydroxy-

Product 1

HCID 233813448-(Benzyloxy)-5-[(2S)oxiranylmethoxy]-3,4-dihydro-2(1H)-quinolinone

Procedure

5,8-Dihydroxy-3,4-dihydro-2(1H)-quinolinone (2.0 g, 11.16 mmol) and potassium carbonate (1.8 g, 13.02 mmol) were stirred at reflux in acetone (35 mL). Benzyl bromide (1.33 mL, 11.2 mmol) was added and refluxing continued for 4 hours. The solvents were removed and the reaction mixture partitioned between chloroform and water. The organic phase was washed with brine and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent evaporated to dryness in vacuo. The residue was purified by flash chromatography on silica gel Merck-60 (eluant: 1:1 hexane-ethyl acetate) to yield the title compound (0.80 g, 2.97 mmol).

Workup

temperaturerefluxing
customThe solvents were removed
customthe reaction mixture partitioned between chloroform and water
washThe organic phase was washed with brine
dry with materialdried over anhydrous magnesium sulfate
filtrationThe solution was filtered
customthe solvent evaporated to dryness in vacuo
customThe residue was purified by flash chromatography on silica gel Merck-60 (eluant: 1:1 hexane-ethyl acetate)

Sources & evidence

ORD record: ord-cd5a3f65fdb34c778448468b6b1fecdd
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06451814B1

Reaction notes

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