Allyl bromide → HCID 58121999, compound

HRID 1808674Notes

Reaction equation

[C:1]1([S:7][C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH2:27](Br)[CH:28]=[CH2:29]>C1COCC1>[C:1]1([S:7][C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:16])[CH2:15][CH2:29][CH:28]=[CH2:27])=[CH:10][CH:9]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: -78 °C

Procedure

20 mmol of 1-(4-(phenyl thio)phenyl)ethanone was dissolved in 100 mL of THF, and cooled at −78° C. To this, 22 mmol of lithium hexamethyldisilazide was added dropwise and stirred for 1 hour. Further, 20 mL of THF solution of 20 mmol of allyl bromide was added dropwise over 10 minutes and a solution temperature was slowly set back to room temperature, and further stirred for 1 hour. Then quenching was carried out with 100 mL of water. An organic layer was extracted with ethylacetate, and washed with an aqueous sodium chloride. Thereafter, the organic layer was concentrated. The thus-obtained mixture was purified by column chromatography (hexane/ethyl acetate=10/1). Thereby, 1-(4-(phenyl thio)phenyl)pent-4-en-1-one having the following structure was obtained with a yield of 52%.

Workup

customwas slowly set back to room temperature
stirringfurther stirred for 1 hour
customThen quenching
extractionAn organic layer was extracted with ethylacetate
washwashed with an aqueous sodium chloride
concentrationThereafter, the organic layer was concentrated
customThe thus-obtained mixture was purified by column chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record: ord-13e194baf351488d81d058728cefa609
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08361681B2

Reaction notes

Loading…