تفاعل #56739

معادلة التفاعل

{(2R)-7-nitro-8-[3-oxo-1-propenyl]-2,3-dihydro-1,4-benzodioxin-2-yl}methyl 4-methylbenzenesulfonate

water

→

title compound

2,3-Dihydro[1,4]dioxino[2,3-f]quinolin-2-ylmethyl 4-methylbenzenesulfonate

المذيبات

acetic acid ethanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe mixture was heated
2. 2
   درجة الحرارةat reflux under nitrogen for 8 hours
3. 3
   ترشيحthe mixture filtered through a pad of celite
4. 4
   استخلاصextracted with ethyl acetate
5. 5
   تجفيفThe extract was dried over magnesium sulfate
6. 6
   ترشيحfiltered
7. 7
   أخرىevaporated in vacuum
8. 8
   أخرىchromatographed on silica gel using a gradient elution commencing with 20% ethyl acetate/hexane

الإجراء التجريبي

To a solution of {(2R)-7-nitro-8-[3-oxo-1-propenyl]-2,3-dihydro-1,4-benzodioxin-2-yl}methyl 4-methylbenzenesulfonate (3.50 g, 8.35 mmole) in 200 mL of acetic acid/ethanol (1:1) was added 2.35 g (42.1 mmole) of iron powder and the mixture was heated at reflux under nitrogen for 8 hours. After the reaction was complete, 150 mL of water was added and the mixture filtered through a pad of celite. The filtrate was neutralized with saturated sodium bicarbonate and extracted with ethyl acetate. The extract was dried over magnesium sulfate, filtered, and evaporated in vacuum. The residue was column chromatographed on silica gel using a gradient elution commencing with 20% ethyl acetate/hexane and ending with 70% ethyl acetate/hexane to give 1.85 g of the (R)-enantiomer of the title compound as a yellow oil. 1H-NMR (CDCl3): doublet 8.8 δ (1 H); doublet: 8.2 δ (1 H); doublet 7.8 δ (2 H); doublet 7.6 δ (1 H); multiplet 7.35 δ (1 H); multiplet 7.25 δ (3 H); multiplet 4.6 δ (1 H); multiplet 4.3-4.4 δ (3 H); multiplet 4.2 δ (1 H); singlet 2.4 δ (3 H).

المصدر