Reaktion #624614

Reaktionsgleichung

2-cyclopropylacetaldehyde

methyl 4-iodobenzoate

isopropylmagnesium chloride lithium chloride

→

(+/−)-methyl 4-(2-cyclopropyl-1-hydroxyethyl)benzoate

Ausbeute 45.4%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe resulting mixture was then stirred at room temperature for 1 hour
2. 2
   SonstigeThe reaction mixture was quenched with saturated ammonium chloride
3. 3
   Sonstigepartitioned between water and ethyl acetate
4. 4
   SonstigeThe layers were separated
5. 5
   Extraktionthe aqueous was extracted again with ethyl acetate
6. 6
   TrocknenThe combined organic layers were dried over sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated
9. 9
   SonstigePurification by column chromatography

Vorschrift

To a −40° C. solution of methyl 4-iodobenzoate (0.39 g, 1.5 mmol) in tetrahydrofuran (7.5 mL) was added isopropylmagnesium chloride-lithium chloride (1.5 mL, 1.3 M in THF, 1.95 mmol) dropwise. After stirring for 30 minutes at −40° C., 2-cyclopropylacetaldehyde (190 mg, 2.26 mmol) was added dropwise. The resulting mixture was then stirred at room temperature for 1 hour. The reaction mixture was quenched with saturated ammonium chloride and partitioned between water and ethyl acetate. The layers were separated and the aqueous was extracted again with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated. Purification by column chromatography gave (+/−)-methyl 4-(2-cyclopropyl-1-hydroxyethyl)benzoate (150 mg, 45%). 1HNMR (400 MHz, CDCl3, δ): 7.89 (d, 2H), 7.32 (d, 2H), 4.75-4.72 (m, 1H), 3.79 (s, 3H), 1.60-1.51 (m, 2H), 0.60-0.51 (m, 1H), 0.49-025 (m, 2H), 0.07-0.12 (m, 2H).

Quelle