反応 #581756

反応方程式

Lithium bis(trimethylsilyl)amide

2-phenyl-propionic acid

1-bromo-3,3-dimethyl-butane

→

clear oil

収率 96.0%

2,5,5-trimethyl-2-phenylhexanoic Acid

収率 96.0%

溶媒

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   温度the resulting solution was cooled in an ice bath
2. 2
   その他The reaction vessel was removed from the cooling bath
3. 3
   その他placed in a 50° C.
4. 4
   濃縮After concentration
5. 5
   workup.DISSOLUTIONthe resulting residue was dissolved in 250 mL of 1 N NaOH
6. 6
   洗浄washed with 250 mL of 2:1 hexane/iso-propyl acetate
7. 7
   抽出extracted with ethyl acetate (3×300 mL)
8. 8
   乾燥The combined organic layers were dried over Na2SO4
9. 9
   濃縮concentrated

実験手順

Lithium bis(trimethylsilyl)amide (32.3 g, 193 mmol) was added to 80 mL of tetrahydrofuran and the resulting solution was cooled in an ice bath. Addition of a solution of 2-phenyl-propionic acid (11.6 g, 77.3 mmol) in 10 mL of tetrahydrofuran to the reaction solution was followed by addition of 1-bromo-3,3-dimethyl-butane (20.4 g, 124 mmol). The reaction vessel was removed from the cooling bath, placed in a 50° C. oil bath, and the reaction solution was stirred for 17 hours. After concentration, the resulting residue was dissolved in 250 mL of 1 N NaOH, washed with 250 mL of 2:1 hexane/iso-propyl acetate, acidified to pH 1 with 6 N HCl, and extracted with ethyl acetate (3×300 mL). The combined organic layers were dried over Na2SO4 and concentrated to give 17.3 g (96%) of clear oil. 1H NMR (300 MHz, CDCl3): δ ppm 0.86 (s, 9H) 1.09 (m, 2H) 1.56 (s, 3H) 1.99 (m, 2H) 7.33 (m, 5H).

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