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

温度

-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レコード

ord-35517808fb2c4f85bbc4e95e78c9c6e4

出典データセット

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07419981B2