Potassium Iodide → 6-(3-Methoxypropoxy)indan-1-one

HRID 922443

Reaction equation

[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.CC1C=CC(S(OC[CH2:24][CH2:25][CH2:26][O:27][CH3:28])(=O)=O)=CC=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[CH3:28][O:27][CH2:26][CH2:25][CH2:24][O:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 6-hydroxyindan-1-one (1.48 g) in acetonitrile (30 mL) were added 4-methoxybutyl 4-methylbenzenesulfonate (2.93 g), potassium iodide (166 mg) and potassium carbonate (2.07 g), and the mixture was heated to stir at 80° C. for 5 hours. To the reaction mixture was added water under ice-cooling, and then the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=7/3), and then triturated with n-hexane/isopropyl ether (2:1) to give 6-(3-methoxypropoxy)indan-1-one [REx(11-1)] (1.1 g) as a colorless powder.

Workup

temperaturethe mixture was heated
temperaturecooling
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated saline
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=7/3)
customtriturated with n-hexane/isopropyl ether (2:1)

Sources & evidence

ORD record: ord-c11c7a90bafb412ab0c1ba6aabc79425
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278944B2

Linked notes

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