反応 #556343

反応方程式

lithium hexamethyldisilazide

sodium bicarbonate water

2-bromo-1,3-dimethylbenzene

pyrrolidine-3-yl methanol hydrochloride

2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl

→

compound

収率 27.8%

(1-(2,6-dimethylphenyl)pyrrolidin-3-yl)methanol

収率 27.8%

溶媒

tetrahydrofuran

ethyl acetate

tetrahydrofuran

反応条件

後処理

1. 1
   その他the resultant reaction mixture
2. 2
   温度was heated
3. 3
   温度refluxed for 2.5 hours
4. 4
   その他the resultant reaction mixture
5. 5
   抽出was extracted with ethyl acetate
6. 6
   洗浄The organic phase was washed with a saturated saline
7. 7
   乾燥was dried over anhydrous sodium sulfate
8. 8
   workup.DISTILLATIONFrom the organic phase, the solvent was distilled off under reduced pressure
9. 9
   その他by purifying the resultant residue by silica gel column chromatography (eluate; n-hexane:ethyl acetate=100:0 to 75:25)
10. 10
    workup.DISTILLATIONfrom the resultant, the solvent was distilled off under reduced pressure

実験手順

To a solution of 2-bromo-1,3-dimethylbenzene (500 mg), pyrrolidine-3-yl methanol hydrochloride (409 mg), bis(dibenzylideneacetone) palladium (155 mg), and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (SPhos; 222 mg) in tetrahydrofuran (5 mL), molecular sieves 4A (powder; 410 mg) were added. To the mixed solution, a solution (8.9 mL) of 1.0 M lithium hexamethyldisilazide in tetrahydrofuran was added, and the resultant reaction mixture was heated and refluxed for 2.5 hours. To the reaction solution, saturated sodium bicarbonate water and ethyl acetate were added, and the resultant reaction mixture was extracted with ethyl acetate. The organic phase was washed with a saturated saline and was dried over anhydrous sodium sulfate. From the organic phase, the solvent was distilled off under reduced pressure, followed by purifying the resultant residue by silica gel column chromatography (eluate; n-hexane:ethyl acetate=100:0 to 75:25), and from the resultant, the solvent was distilled off under reduced pressure to obtain the subject compound (154 mg) as a yellow oily substance.

出典