Methanol → 1-(5-Methoxy-3-methyl-1-benzofuran-2-yl)-5-(methylsulfanyl)pentan-1-one

HRID 2091233Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:11]=2[C:12]=1[CH3:13])=[O:7].CO.O1CCCC1.[CH3:27][S-:28].[Na+]>O>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:10]2[O:9][C:8]([C:6](=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2][S:28][CH3:27])=[C:12]([CH3:13])[C:11]=2[CH:14]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of 5-chloro-1-(5-methoxy-3-methyl-1-benzofuran-2-yl)pentan-1-one (1.30 g) synthesized above, methanol (15 mL) and tetrahydrofuran (15 mL) was added a 15% aqueous solution (4.33 mL) of sodium methanethiolate, and the mixture was stirred at room temperature for 1 hr and at 50° C. for 1 hr. Sodium methanethiolate (325 mg) was additionally added and the mixture was stirred at 50° C. for 1 hr. Sodium methanethiolate (325 mg) was additionally added again, and the mixture was stirred at 50° C. for 1 hr. Water was added to quench the reaction, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was washed with hexane to give the title object compound (492 mg, 36%) as a yellow solid.

Workup

stirringthe mixture was stirred at 50° C. for 1 hr
stirringthe mixture was stirred at 50° C. for 1 hr
customto quench
customthe reaction
extractionthe reaction mixture was extracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
washThe residue was washed with hexane

Sources & evidence

ORD record: ord-ca883e23bb3640bc828a6f02d2fd23e7
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436043B2

Reaction notes

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