Réaction #56724

Équation de réaction

t-butyl acetate

diisopropyl amine

nBuLi

(R)-1-iodo-2,6-dimethyl heptane

→

(4R)-4,8-dimethyl nonanoic acid t-butyl ester

Rendement 87.4%

Solvants

THF

pentane

THF

HMPA

Conditions de réaction

Traitement

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
   Autreallowed to slowly reach ambient temperature overnight
4. 4
   Températureheated at 35° C.
5. 5
   Autrethe reaction to completion
6. 6
   AutreThe reaction was quenched by the addition of ammonium chloride (saturated aqueous solution)
7. 7
   Extractionthe mixture was extracted with EtOAc (2×10 mL)
8. 8
   Lavagewashed with water
9. 9
   Séchagedried (MgSO4)
10. 10
    Filtrationfiltered
11. 11
    Concentrationconcentrated

Mode opératoire

To diisopropyl amine (0.827 mL, 5.9 mmol) in THF (8 mL) at −78° C. was added nBuLi (2.65 mL of a 2.6 M solution in pentane). The solution was stirred for 30 min at −78° C., followed by the addition of t-butyl acetate (0.8 mL, 5.9 mmol). The mixture was stirred at −78° C. for 2 h, and then (R)-1-iodo-2,6-dimethyl heptane (0.3 g, 1.18 mmol) and HMPA (1.5 mL) in THF (1 mL) was added. The reaction was stirred at −78° C. and allowed to slowly reach ambient temperature overnight, then heated at 35° C. to drive the reaction to completion. 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 (98/2 hexane/EtOAc) provided 0.25 g of (4R)-4,8-dimethyl nonanoic acid t-butyl ester.

Source