تفاعل #6587

معادلة التفاعل

phenylacetylene

N-methoxy-N-methylbenzamide

lithium diisopropylamide

tetrahydrofuran

→

title compound

المردود 61.4%

1-Phenyl-3-phenyl-2-propyne-1-one

المردود 61.4%

المذيبات

cyclohexane

ظروف التفاعل

المعالجة

1. 1
   أخرىRemove the cooling bath
2. 2
   درجة الحرارةCool the yellow solution to 0° C.
3. 3
   أخرىRemove the cooling bath
4. 4
   workup.STIRRINGstir for 30 minutes at room temperature
5. 5
   workup.ADDITIONPour onto ethyl ether and water
6. 6
   أخرىseparate the organic phase
7. 7
   تجفيفdry (MgSO4)
8. 8
   ترشيحFilter
9. 9
   أخرىevaporate the solvent in vacuo
10. 10
    أخرىto yield an oil
11. 11
    أخرىPurify by silica gel chromatography (2% ethyl acetate/hexane)
12. 12
    workup.DISTILLATIONthen purify further by distillation (2×)

الإجراء التجريبي

Place lithium diisopropylamide (10 mL of a 1.5M solution in cyclohexane) and tetrahydrofuran (40 mL) under an argon atmosphere and cool to 0° C. Add, by dropwise addition, phenylacetylene (1.65 mL, 15 mmol). Remove the cooling bath and stir for 30 minutes as room temperature. Cool the yellow solution to 0° C. and add, by dropwise addition, N-methoxy-N-methylbenzamide (3.04 mL, 20 mmol). Remove the cooling bath and stir for 30 minutes at room temperature. Pour onto ethyl ether and water, separate the organic phase and dry (MgSO4). Filter and evaporate the solvent in vacuo to yield an oil. Purify by silica gel chromatography (2% ethyl acetate/hexane) then purify further by distillation (2×) to yield 1.9 g of the title compound; bp 210° C. in vacuo.

المصدر