3-(Methylthio)-1-propanol → 2-(3-Methylsulfanyl-propoxy)-isoindole-1,3-dione

3-Methylsulfanyl-propan-1-ol (4.133 g, 38.92 mmol) was dissolved in THF (anhydrous, 100 mL). To this solution, triphenylphosphine (10.2 g, 38.92 mmol) and N-hydroxyphthalimide (6.4 mg, 38.92 mmol) were added and dissolved with stirring. Diisopropyl azodicarboxylate (8.5 mL, 42.812 mmol) was added dropwise thereto with cooling the reaction vessel in an ice-bath under nitrogen atmosphere. The reaction mixture was warmed to room temperature, and stirred for 5 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and triturated with diethyl ether:hexane (1:1, about 100 ml) to precipitate triphenylphosphine oxide as a white solid, which was filtered off. The filtrate was concentrated under reduced pressure to give a yellow oily residue. The resultant yellow oil was purified by silica gel flash chromatography (BW300, Fuji Silysia Chemical, 20% ethyl acetate/hexane as an eluent) to give 2-(3-methylsulfanyl-propoxy)-isoindole-1,3-dione (6.4 g, 65%).

1. dissolutiondissolved
2. temperaturewith cooling the reaction vessel in an ice-bath under nitrogen atmosphere
3. stirringstirred for 5 hours
4. customAfter completion of the reaction
5. concentrationthe reaction mixture was concentrated under reduced pressure
6. customtriturated with diethyl ether:hexane (1:1, about 100 ml)
7. customto precipitate triphenylphosphine oxide as a white solid, which
8. filtrationwas filtered off
9. concentrationThe filtrate was concentrated under reduced pressure
10. customto give a yellow oily residue
11. customThe resultant yellow oil was purified by silica gel flash chromatography (BW300, Fuji Silysia Chemical, 20% ethyl acetate/hexane as an eluent)

ORD 기록

ord-da442fe9c3494a84b96c52bc1aad841c

출처 데이터셋

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07745663B2