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

Temperature

-78 °C

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.

1. stirringThe mixture was stirred at −78° C. for 2 h
2. stirringThe reaction was stirred at −78° C.
3. waitallowed to slowly reach ambient temperature over 16 h
4. customThe reaction was quenched by the addition of ammonium chloride (saturated aqueous solution)
5. extractionthe mixture was extracted with EtOAc (2×10 mL)
6. washwashed with water
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-d39673d44a37418fa73257d382656777

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07112610B2