Reaktion #363316

Reaktionsgleichung

Methyl 1-n-butyl-5-(4-chloro-2-methoxymethoxyphenyl)-1H-pyrazol-4-yl carboxylate

Dibal-H

→

title compound

Ausbeute 104.5%

1-n-Butyl-5-(4-chloro-2-methoxymethoxyphenyl)-4-hydroxymethylpyrazole

Ausbeute 104.5%

Lösungsmittel

CH2Cl2

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction was quenched with MeOH (100 mL)
2. 2
   workup.ADDITIONfollowed by addition of 35 mL of conc. HCl in 200 mL of water
3. 3
   Extraktionextracted with CH2Cl2 (3×200 mL)
4. 4
   WaschenThe combined organic extracts were washed with brine
5. 5
   Trocknendried (Na2SO4)
6. 6
   SonstigeRemoval of the solvent under reduced pressure

Vorschrift

To a solution of Methyl 1-n-butyl-5-(4-chloro-2-methoxymethoxyphenyl)-1H-pyrazol-4-yl carboxylate (10.00 g, 0.028 mol) in 200 mL of CH2Cl2 at 0° C. was added 85.2 mL of 1.5 M Dibal-H in toluene. After string for 1 h, the reaction was quenched with MeOH (100 mL) followed by addition of 35 mL of conc. HCl in 200 mL of water. The resulting mixture was stirred for 15 min. and extracted with CH2Cl2 (3×200 mL). The combined organic extracts were washed with brine and dried (Na2SO4). Removal of the solvent under reduced pressure gave 9.50 g (97%) of the title compound as a oil: MS (ESI) m/z 325 (M+H)+; 1H NMR (400 MHz, CDCl3) d 7.63 (s, 1H), 7.13-7.29 (m, 3H), 5.09 (s, 2H), 4.36 (dd, 2H). 3.80-3.98 (m, 2H), 3.35 (s, 3H), 1.70 (m, 2H), 1.18 (m, 2H), 0.81 (t, 3H).

Quelle