Tetrahydrofuran → 4-(Methanesulfinyl)-4-(methylsulfanyl)cyclopent-1-ene

Formaldehyde dimethyl mercaptal S-oxide (3.170g) was dissolved in 30 ml. of tetrahydrofuran, and at -15° C., 20 ml. of an n-hexane solution (1.3 millimols/milliliter) of n-butyl lithium was added. The mixture was stirred for 30 minutes at -15° to -5° C., and then 1.455g of cis-1,4-dichloro-2-butene was added. The mixture was stirred for 2.5 hours at -70° C. and then for 1.5 hours at room temperature. Methylene chloride (100 ml) and 30 ml. of water were added, and the mixture was shaken. The organic phase was separated, and the aqueous phase was extracted four times with 50 ml. of methylene chloride each time. The extract and the organic phase were combined, and dried with anhydrous sodium sulfate. The dried mixture was concentrated at reduced pressure, and the residue was separated by column chromatography (Florisil, eluted with methylene chloride and ethyl acetate) to afford 1.560 g of 3-cyclopentenone dimethyl mercaptal S-oxide and a light yellow oily substance in a yield of 76%.

1. customat -15° C.
2. stirringThe mixture was stirred for 2.5 hours at -70° C.
3. waitfor 1.5 hours at room temperature
4. stirringthe mixture was shaken
5. customThe organic phase was separated
6. extractionthe aqueous phase was extracted four times with 50 ml
7. extractionThe extract
8. dry with materialdried with anhydrous sodium sulfate
9. concentrationThe dried mixture was concentrated at reduced pressure
10. customthe residue was separated by column chromatography (Florisil, eluted with methylene chloride and ethyl acetate)

ORD record

ord-11b3fe8f03ff45b69c282642d6a7a81b

Source dataset

uspto-grants-1977_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04020171