반응 #1884948
ord-430a39f084344f4cab3af2b7f7ac5818
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후처리
- 1기타The mixture was purged with argon for 10 minutes
- 2workup.ADDITIONfollowed by the slow addition of solid potassium hydroxide (2 g)
- 3workup.ADDITIONThe mixture was then poured into de-ionized water (150 mL)
- 4추출the organic phase extracted with diethyl ether (4×100 mL)
- 5기타The organic phases were collected
- 6세척washed with brine (100 mL)
- 7건조The organic phase was dried over magnesium sulphate
- 8여과filtered
- 9농축concentrated
- 10기타to give the crude product as yellow oil
- 11기타Purification via flash chromatography with hexanes (monitored at 254 nm, collected at 320 nm)
- 12기타drying under high vacuum for 48 hours
- 13기타gave pure product as colorless oil
실험 절차
To a solution of 4H-Cyclopenta[2,1-b:3,4-b′]dithiophene (CDT) (1.63 g, 9.14 mmol) in dimethyl sulfoxide (50 mL) was added hexyl bromide (3.1 g, 18.9 mmol) and a catalytic amount of potassium iodide (50 mg). The mixture was purged with argon for 10 minutes followed by the slow addition of solid potassium hydroxide (2 g). The now dark green mixture was stirred in the dark at room temperature for 72 hours. The mixture was then poured into de-ionized water (150 mL) and the organic phase extracted with diethyl ether (4×100 mL). The organic phases were collected and washed with brine (100 mL) and a saturated ammonium chloride solution (100 mL). The organic phase was dried over magnesium sulphate, filtered, and concentrated to give the crude product as yellow oil. Purification via flash chromatography with hexanes (monitored at 254 nm, collected at 320 nm) and drying under high vacuum for 48 hours gave pure product as colorless oil. Yield 2.8 g (88%). 1H NMR (500 MHz, CDCl3): δ=7.15 (d, 2H, 3JH-H=5 Hz), 6.94 (d, 2H, 3JH-H=5 Hz), 1.84 (m, 4H, C—CH2), 1.19 (m, 12H, alkyl-CH2), 0.95 (m, 4H, alkyl-CH2), 0.82 (m, 6H, alkyl-CH3).