Reaktion #1109471

Reaktionsgleichung

compound 30

(R)-METHYL 3-HYDROXYTETRADECANOATE

4-methoxybenzyl trichloroacetimidate

camphorsulfonic acid

→

product 32

Ausbeute 82.1%

(R)-METHYL 3-(4-METHOXYBENZYLOXY)TETRADECANOATE

Ausbeute 82.1%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe mixture was washed with a saturated solution of NaHCO3 (300 mL) and water (300 mL)
2. 2
   Trocknendried over Na2SO4
3. 3
   SonstigeThe drying agent was removed by filtration
4. 4
   Sonstigethe solvents removed
5. 5
   Sonstigea rotary evaporator
6. 6
   SonstigeThe residue was purified by chromatography on silica gel (120 g RediSep column
7. 7
   Wascheneluting with a gradient of 0% through 30% ethyl acetate/hexanes over 70 min

Vorschrift

To a solution of compound 30 (3.50 g, 12.9 mmol) and 4-methoxybenzyl trichloroacetimidate (4.65 g, 17.3 mmol) in DCM (100 mL) was added camphorsulfonic acid (450 mg, 1.92 mmol). The mixture was stirred overnight at room temperature. The mixture was washed with a saturated solution of NaHCO3 (300 mL) and water (300 mL) and dried over Na2SO4. The drying agent was removed by filtration and the solvents removed using a rotary evaporator. The residue was purified by chromatography on silica gel (120 g RediSep column, eluting with a gradient of 0% through 30% ethyl acetate/hexanes over 70 min, 85 mL/min) to give the product 32 (4.01 g, 81%) as a colorless liquid.

Quelle