Reaction #56727

Reaction equation

methyl isobutyrate

diisopropyl amine

nBuLi

1-iodo-4-methyl pentane

DMPU

→

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

Yield 99.4%

Solvents

THF

hexane

THF

Conditions

Workup

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
   OtherThe reaction was quenched by the addition of ammonium chloride (saturated aqueous solution)
5. 5
   Extractionthe mixture was extracted with EtOAc (2×10 mL)
6. 6
   Washwashed with water
7. 7
   Dryingdried (MgSO4)
8. 8
   Filtrationfiltered
9. 9
   Concentrationconcentrated

Procedure

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.

Source