تفاعل #745014

معادلة التفاعل

N,N-Diisopropylethylamine

methyl 2,2-dimethyl-3-hydroxypropionate

Methanethiol sodium salt

Methane sulfonyl chloride

→

title compound

المردود 24.0%

2,2-Dimethyl-3-methylsulfanyl-propionic acid methyl ester

المردود 24.0%

المذيبات

dichloromethane

hydrochloric acid

dioxan

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   أخرىthe layers were separated
2. 2
   استخلاصThe aqueous was extracted with dichloromethane (2×50 mL)
3. 3
   تجفيفthe combined organic solution was dried over magnesium sulfate
4. 4
   تركيزconcentrated in vacuo
5. 5
   درجة الحرارةthe mixture was heated
6. 6
   درجة الحرارةunder reflux for 24 hours
7. 7
   غسيلwashed with water and brine
8. 8
   تجفيفdried over magnesium sulfate
9. 9
   تركيزconcentrated in vacuo
10. 10
    أخرىPurification by column chromatography on silica gel
11. 11
    غسيلeluting with dichloromethane:pentane 50:50 to 100:0

الإجراء التجريبي

N,N-Diisopropylethylamine (15.5 g, 0.12 mol) was added to a solution of methyl 2,2-dimethyl-3-hydroxypropionate (13.2 g, 0.1 mol) in dichloromethane (150 mL) and the solution was cooled to 0° C. Methane sulfonyl chloride (12.6 g, 0.11 mol) was then added dropwise and the mixture was stirred at 0° C. for 90 minutes. The reaction mixture was then diluted with 0.5M hydrochloric acid (100 mL) and the layers were separated. The aqueous was extracted with dichloromethane (2×50 mL) and the combined organic solution was dried over magnesium sulfate and concentrated in vacuo. Methanethiol sodium salt (7.7 g, 0.11 mol) was added to a solution of the residue in dioxan (100 mL) and the mixture was heated under reflux for 24 hours. The mixture was then diluted with ethyl acetate (250 mL), washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography on silica gel, eluting with dichloromethane:pentane 50:50 to 100:0, afforded the title compound as a pale yellow oil in 24% yield, 3.85 g.

المصدر