Electric Literature of 2436-29-5,Some common heterocyclic compound, 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, molecular formula is C11H9NO3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Into a heat-vacuum dried 50 mL recovery flask, DMF (13 mL), 3-phthalimidylpropanal (manufactured by Aurora Fine Chemicals, 266.0 mg, 1.13 mmol, 1 equivalent), N,N-diallylthioacetamide (244 muL, 1.35 mmol, 1.2 equivalents), and the Cu/(S,S)-Ph-BPE solution prepared as above (100 muL, 0.10 mmol, 0.09 equivalent) were added under an argon atmosphere. The recovery flask was transferred to a constant temperature bath of -40C, and the THF solution of 2,2,5,7,8-pentamethylchromanol lithium salt prepared as above (50 muL, 0.10 mmol, 0.09 equivalent) was added, followed by stirring at -40C for 24 hours. Subsequently, a saturated aqueous solution of ammonium chloride (5 mL) and 2,2-bipyridine (15.6 mg, 0.10 mmol, 0.09 equivalent) were added, and the resulting mixture was extracted three times with ethyl acetate (5 mL). The resulting organic layer was sequentially washed with distilled water, saturated sodium bicarbonate water, and saturated brine, and then dried over anhydrous sodium sulphate. After filtration and concentration, the residue thus obtained was purified by flash column chromatography (hexane/ethyl acetate = 7/1 to 2/1 (volume ratio)) to obtain the following thioamide compound A-4 as a yellow oily matter. Yield 251.1 mg (62%, 75%ee).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(1,3-Dioxoisoindolin-2-yl)propanal, its application will become more common.
Reference:
Patent; Microbial Chemistry Research Foundation; SHIBASAKI, Masakatsu; KUMAGAI, Naoya; EP2679580; (2014); A1;,
Indoline – Wikipedia,
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