反応 #56727

反応方程式

methyl isobutyrate

diisopropyl amine

nBuLi

1-iodo-4-methyl pentane

DMPU

→

2,2,6-Trimethyl-heptanoic acid methyl ester

収率 99.4%

溶媒

THF

hexane

THF

反応条件

後処理

1. 1
   workup.STIRRINGThe mixture was stirred at −78° C. for 2 h
2. 2
   workup.STIRRINGThe reaction was stirred at −78° C.
3. 3
   workup.WAITallowed to slowly reach ambient temperature over 16 h
4. 4
   その他The reaction was quenched by the addition of ammonium chloride (saturated aqueous solution)
5. 5
   抽出the mixture was extracted with EtOAc (2×10 mL)
6. 6
   洗浄washed with water
7. 7
   乾燥dried (MgSO4)
8. 8
   ろ過filtered
9. 9
   濃縮concentrated

実験手順

To diisopropyl amine (1.54 mL, 11.03 mmol) in THF (22 mL) at −78° C. was added nBuLi (6.89 mL of a 1.6 M solution in hexane). The solution was stirred for 30 min at −78° C., followed by the addition of methyl isobutyrate (0.97 mL, 8.48 mmol). The mixture was stirred at −78° C. for 2 h, and then 1-iodo-4-methyl pentane (1.8 g, 8.48 mmol) and DMPU (0.55 mL, 4.24 mmol) in THF (6 mL) was added. The reaction was stirred at −78° C. and allowed to slowly reach ambient temperature over 16 h. The reaction was quenched by the addition of ammonium chloride (saturated aqueous solution), and the mixture was extracted with EtOAc (2×10 mL). The organics were combined, washed with water, dried (MgSO4), filtered and concentrated. Silica gel chromatography (99/1 hexane/EtOAc) provided 1.57 g of 2,2,6-Trimethyl-heptanoic acid methyl ester.

出典