تفاعل #587289

معادلة التفاعل

triethylamine

dimethyl sulfoxide

oxalyl chloride

4-methoxybenzenepropanol

→

desired product

المردود 51.0%

3-(4-Methoxyphenyl)propanal

المردود 51.0%

المذيبات

dichloromethane

dichloromethane

dichloromethane

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONUpon completion of the addition
2. 2
   workup.STIRRINGThe resulting mixture was stirred at −78° C. for 40 min
3. 3
   درجة الحرارةto warm to 0° C.
4. 4
   workup.STIRRINGstirred at this temperature for 1 hour
5. 5
   أخرىquenched with water (15 mL)
6. 6
   أخرىThe organic extracts were separated
7. 7
   غسيلwashed with water and brine
8. 8
   تجفيفdried over magnesium sulfate
9. 9
   ترشيحfiltered
10. 10
    تركيزconcentrated under reduced pressure
11. 11
    أخرىThe residue was purified by flash chromatography
12. 12
    غسيلeluting with ethyl acetate in hexanes (gradient: 3 min: 0/100 to 23 min: 20/80)

الإجراء التجريبي

A solution of dimethyl sulfoxide (5.1 mL) in dichloromethane (10 ml) was added to a stirred solution of oxalyl chloride (3.0 mL, 36 mmol) in dichloromethane (40 ml) at −78° C. over 30 min. Upon completion of the addition, the mixture was stirred at −78° C. for 5 min, followed by addition of a solution of 4-methoxybenzenepropanol (3.0 g, 18 mmol) in dichloromethane (20 ml) at −78° C. over 30 min. The resulting mixture was stirred at −78° C. for 40 min. Next, triethylamine (15 mL, 110 mmol) was added dropwise over 10 min. The resulting mixture was allowed to warm to 0° C. and stirred at this temperature for 1 hour. It was diluted with dichloromethane (30 mL) and quenched with water (15 mL). The organic extracts were separated, washed with water and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography eluting with ethyl acetate in hexanes (gradient: 3 min: 0/100 to 23 min: 20/80) to afford the desired product (1.50 g, 51%).

المصدر