Oxalyl chloride → 7-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-one

4-(4-Phenylsulfanyl-phenyl)-butyric acid (5.0 g, 18.4 mmol) was dissolved in 50 mL tetrahydrofuran (THF). Oxalyl chloride (1.8 mL, 20 mmol) and one drop of DMF were added, and the reaction mixture was stirred for 1 hour, and then evaporated to dryness under reduced pressure. The resulting residue was dissolved in 40 mL of 1,2-dichloroethane, and aluminum trichloride (0.85 g, 25 mmol) was added all at once. The reaction mixture was stirred for 1 hour, and quenched by addition of 2% HCl. This aqueous mixture was extracted twice with 100 mL of EtOAc, and the combined organic layers were dried (MgSO4) and evaporated to yield 2.54 g (10 mmol, 55.5%) of 7-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-one as a gummy residue. MS: 255 (M+H)+.

1. customevaporated to dryness under reduced pressure
2. dissolutionThe resulting residue was dissolved in 40 mL of 1,2-dichloroethane
3. stirringThe reaction mixture was stirred for 1 hour
4. customquenched by addition of 2% HCl
5. extractionThis aqueous mixture was extracted twice with 100 mL of EtOAc
6. dry with materialthe combined organic layers were dried (MgSO4)
7. customevaporated

ORD 기록

ord-d07e1b336e4d463ba52527aea6841d39

출처 데이터셋

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08093424B2