Réaction #820271

Équation de réaction

diisopropylamine

n-butyl lithium

diiodomethane

tert-butyl cyclopropanecarboxylate

NH4Cl

→

title compound

Rendement 14.6%

tert-Butyl 1-(iodomethyl)cyclopropanecarboxylate

Rendement 14.6%

Solvants

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was cooled to −78° C.
2. 2
   workup.STIRRINGthe mixture was stirred for 3 h
3. 3
   Températureto warm up to room temperature overnight
4. 4
   Extractionwas extracted with diethyl ether (50 mL)
5. 5
   Lavagewashed with brine (20 mL)
6. 6
   Séchagedried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated
9. 9
   Autreto give brown oil
10. 10
    AutreThe oil was chromatographed on a column of silica gel eluting with hexane/diethyl ether (40:1)

Mode opératoire

To a stirred solution of diisopropylamine (7.7 mL, 0.055 mol) in tetrahydrofuran (80 mL), n-butyl lithium (1.59 M in cyclohexane, 34 mL, 0.055 mol) was added slowly at −70° C. and the mixture was stirred for 20 min at 0° C. The mixture was cooled to −78° C. and tert-butyl cyclopropanecarboxylate (6.5 g, 0.046 mol, Kohlrausch et al., Z. Elektrochem. Angew. Phys. Chem., 1937, 70, 392) in tetrahydrofuran (10 mL) was added dropwise, and the mixture was stirred for 3 h. Then, diiodomethane (4.0 mL, 0.050 mol) in tetrahydrofuran (10 mL) was added dropwise, and the mixture was allowed to warm up to room temperature overnight. Saturated aqueous NH4Cl (80 mL) was added to the solution and it was extracted with diethyl ether (50 mL), washed with brine (20 mL), dried over MgSO4, filtered and concentrated to give brown oil. The oil was chromatographed on a column of silica gel eluting with hexane/diethyl ether (40:1) to give 1.9 g of the title compound as a crude product. The crude product was used without further purification. Rf: 0.3 (hexane/diethyl ether (40:1))

Source