تفاعل #2146743

معادلة التفاعل

(3R,4R,5R)-5-(2,4-dichloro-benzyloxymethyl)-4-(2,4-dichlorobenzyloxy)-2-methoxy-tetrahydrofuran-3-acetate

NaOMe

→

(3R,4S,5R)-5-(2,4-Dichlorobenzyloxymethyl)-4-(2,4-dichlorobenzyloxy)-2-methoxy-tetrahydrofuran-3-ol

المذيبات

MeOH

MeOH

ظروف التفاعل

المعالجة

1. 1
   تركيزThe reaction mixture is concentrated
2. 2
   workup.DISSOLUTIONdissolved in ethyl acetate (180 ml)
3. 3
   غسيلwashed with 1 N HCl solution and saturated brine
4. 4
   تجفيفdried (anhyd Na2SO4)
5. 5
   تركيزconcentrated

الإجراء التجريبي

To a solution of (3R,4R,5R)-5-(2,4-dichloro-benzyloxymethyl)-4-(2,4-dichlorobenzyloxy)-2-methoxy-tetrahydrofuran-3-acetate I-1 (10 g, 19.1 mmol) in MeOH (150 ml) is added a solution of 30% NaOMe in MeOH (5.37 ml, 28.6 mmol, 1.5 equiv.) and the reaction is stirred at room temperature for 30 mins. The reaction mixture is concentrated and dissolved in ethyl acetate (180 ml), washed with 1 N HCl solution and saturated brine, dried (anhyd Na2SO4) and concentrated to give (3R,4S,5R)-5-(2,4-Dichlorobenzyloxymethyl)-4-(2,4-dichlorobenzyloxy)-2-methoxy-tetrahydrofuran-3-ol I-2 as yellowish oil. The obtained crude compound is used for the next step without further purification.

المصدر