Diisobutylaluminum hydride → 2,2,6-Trimethyl-heptan-1-ol

Temperature

-78 °C

2,2,6-Trimethyl-heptanoic acid methyl ester (1.97 g, 10.6 mmol) was taken up in toluene (65 mL) and cooled to −78° C. DiBALH (12.7 mL of a 1 N solution in toluene) was added dropwise. After 45 min, 1.5 mL DiBALH was added. After 2 h, the reaction was quenched by the addition of 15 mL MeOH at −78° C. The mixture was warmed to ambient temperature, and then cooled again to −78° C. for the addition of 10 mL 1 N HCl. The mixture was extracted with EtOAc (3×15 mL). The combined organics were washed with brine, dried (MgSO4), filtered and concentrated. The residual oil was purified via silica gel chromatography (95/5 Hexane/EtOAc) to give 2,2,6-Trimethyl-heptan-1-ol (0.88 g). m/z 159 (M+).

1. waitAfter 2 h
2. customthe reaction was quenched by the addition of 15 mL MeOH at −78° C
3. temperatureThe mixture was warmed to ambient temperature
4. temperaturecooled again to −78° C. for the addition of 10 mL 1 N HCl
5. extractionThe mixture was extracted with EtOAc (3×15 mL)
6. washThe combined organics were washed with brine
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated
10. customThe residual oil was purified via silica gel chromatography (95/5 Hexane/EtOAc)

ORD record

ord-5a06f68ebf554e61a82e2e61a4ea6975

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07419981B2