反応 #216974

反応方程式

diisopropylazodicarboxylate

4-propylphenol

6-bromo-1-hexanol

triphenylphosphine

triphenylphosphine

diisopropylazodicarboxylate

→

title compound

収率 67.0%

1-[(6-Bromohexyl)oxy]-4-propylbenzene

収率 67.0%

溶媒

THF

THF

反応条件

後処理

1. 1
   その他The slightly yellow reaction
2. 2
   workup.ADDITIONwas added
3. 3
   workup.ADDITIONwas added
4. 4
   濃縮The mixture was concentrated in vacuo
5. 5
   その他the white powder obtained
6. 6
   その他was purified by flash chromatography on silica gel (150 g)
7. 7
   洗浄eluted with a step gradient of hexane to 2:98 EtOAc/hexane
8. 8
   その他The slightly impure product obtained
9. 9
   その他was rechromatographed on silica gel (150 g)
10. 10
    洗浄eluted with 1:99 EtOAc/hexane

実験手順

A solution of diisopropylazodicarboxylate (2.12 g, 10.5 mmol) in THF (25 mL) was added via syringe pump over 1.5 h to a mixture of 4-propylphenol (purchased from Aldrich Chemical Co.) (1.36 g, 10.0 mmol), 6-bromo-1-hexanol (purchased from Aldrich Chemical Co.) (1.81 g, 10.0 mmol), and triphenylphosphine (2.75 g, 10.5 mmol) in THF (25 mL) at 0° C. under argon. The slightly yellow reaction was stirred at 0° C. for 30 min, whereupon additional triphenylphosphine (262 mg, 1.00 mmol) was added, followed by addition of diisopropylazodicarboxylate (200 mL, 1.0 mmol) over 30 min. The reaction was allowed to warm to RT, at which time silica gel (15 g) was added. The mixture was concentrated in vacuo and the white powder obtained was purified by flash chromatography on silica gel (150 g) eluted with a step gradient of hexane to 2:98 EtOAc/hexane. The slightly impure product obtained was rechromatographed on silica gel (150 g) eluted with 1:99 EtOAc/hexane to give title compound (2.00 g, 67%) as a colorless oil.

出典