تفاعل #49871

معادلة التفاعل

ethyl 1-methyl-5-(phenylmethoxy)-1H-indole-2-carboxylate

isopropylmagnesium chloride

ether

thionyl chloride

→

product

المردود 53.0%

Ethyl 1-methyl-3-[(1-methylethyl)sulfinyl]-5-(phenylmethoxy)-1H-indole-2-carboxylate

المردود 53.0%

المذيبات

hexane

chloroform

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITis continued for 30 minutes
3. 3
   ترشيحThe crude indole sulfinyl chloride intermediate is filtered
4. 4
   غسيلwashed with hexane
5. 5
   workup.DISSOLUTIONdissolved in 200 mL of tetrahydrofuran
6. 6
   workup.STIRRINGAfter stirring for 15 minutes
7. 7
   أخرىthe reaction mixture is quenched by the dropwise addition of 20 mL of 2.0N HCl
8. 8
   درجة الحرارةThe reaction mixture is warmed to room temperature
9. 9
   workup.ADDITIONdiluted with water
10. 10
    استخلاصextracted with ethyl acetate
11. 11
    غسيلThe combined organic layers are washed with brine
12. 12
    تجفيفdried (anhydrous magnesium sulfate)
13. 13
    أخرىevaporated
14. 14
    أخرىThe residue is triturated with ether
15. 15
    أخرىto give a solid which
16. 16
    أخرىis recrystallized from aqueous methanol

الإجراء التجريبي

A slurry of ethyl 1-methyl-5-(phenylmethoxy)-1H-indole-2-carboxylate (10.0 g, 32 mmol; Monge Vega A, et al., An. Ouim. 1976;72:267) in 30 mL of chloroform is treated dropwise with thionyl chloride (9.5 mL, 15.5 g, 130 mmol). After stirring for 20 minutes, 90 mL of hexane is added, and stirring is continued for 30 minutes. The crude indole sulfinyl chloride intermediate is filtered, washed with hexane, and dissolved in 200 mL of tetrahydrofuran. The solution is cooled to -78° C. and treated dropwise with a 2.0M solution of isopropylmagnesium chloride in ether (16.4 mL, 32.8 mmol). After stirring for 15 minutes, the reaction mixture is quenched by the dropwise addition of 20 mL of 2.0N HCl. The reaction mixture is warmed to room temperature, diluted with water, and extracted with ethyl acetate. The combined organic layers are washed with brine, dried (anhydrous magnesium sulfate), and evaporated. The residue is triturated with ether to give a solid which is recrystallized from aqueous methanol to yield 6.8 g (53%) of product; mp 142°-145° C.

المصدر