Hydrochloric Acid → 3-Chloro-1-(5,5-dimethyl-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl)propan-1-one

온도

-70 °C

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer was purged with nitrogen and charged with 106d (2.41 g, 10.0 mmol) and anhydrous THF (20 mL). The solution was cooled to −70° C., and 1 M vinylmagnesium bromide in THF (11 mL, 11.0 mmol) was added with the reaction temperature maintained below −60° C. The reaction mixture was stirred at −13 to −7° C. for 2 h and then warmed to room temperature over 30 min. The reaction was again cooled to −70° C., and a 2 M solution of hydrogen chloride in ether (22.5 ml, 45 mmol) was added. The reaction was then stored in a freezer at −10° C. overnight. After this time the mixture was evaporated under reduced pressure on a rotary evaporator, and the resulting residue partitioned between water (100 mL) and ether (100 mL). The ether extract was dried over sodium sulfate and evaporated under reduced pressure on a rotary evaporator to afford crude 106e (2.86 g, 118%) as a brown oil with approximately 75% purity (by NMR): 1H NMR (300 MHz, CDCl3) δ 7.45 (s, 1H), 3.89 (t, 2H, J=6.9 Hz), 3.30 (t, 2H, J=6.9 Hz), 2.75 (s, 2H), 2.59 (s, 2H), 1.24 (s, 6H)

1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer
2. customwas purged with nitrogen
3. temperaturemaintained below −60° C
4. temperaturewarmed to room temperature over 30 min
5. temperatureThe reaction was again cooled to −70° C.
6. waitThe reaction was then stored in a freezer at −10° C. overnight
7. customAfter this time the mixture was evaporated under reduced pressure on a rotary evaporator
8. customthe resulting residue partitioned between water (100 mL) and ether (100 mL)
9. extractionThe ether extract
10. dry with materialwas dried over sodium sulfate
11. customevaporated under reduced pressure on a rotary evaporator

ORD 기록

ord-10affe8fdbe94e5281ffdec2173800d4

출처 데이터셋

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09238655B2