반응 #164817

반응 방정식

Hydrochloric acid

2,4-pentanedione

2,4-Pentanedione

benzaldehyde

tributyl borate

Butylamine

→

yellow solid

수율 162.8%

1,7-Diphenyl-1,6-heptadiene-3,5-dione

수율 162.8%

용매

ethyl acetate

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture stirred for 15 min at room temperature
2. 2
   workup.STIRRINGstirring
3. 3
   workup.WAITwas continued for 18 hr at room temperature
4. 4
   workup.ADDITIONadded to the mixture
5. 5
   workup.STIRRINGstirring
6. 6
   workup.WAITwas continued for 1 hr
7. 7
   추출The resulting mixture was extracted into ethyl acetate
8. 8
   세척washed with saturated sodium chloride
9. 9
   건조dried over magnesium sulfate
10. 10
    여과filtered
11. 11
    기타evaporated
12. 12
    기타to afford a solid
13. 13
    기타The crude solid was triturated with methanol

실험 절차

Boric anhydride (0.49 g, 7.0 mmol) was combined with 2,4-pentanedione (2, 1.05 ml, 10.0 mmol) and stirred for 18 hr at room temperature under a nitrogen atmosphere. A solution of dry ethyl acetate (10 ml), benzaldehyde (1b, 2.05 g, 20.2 mmol) and tributyl borate (11.00 ml, 40.5 mmol) was added and the mixture stirred for 15 min at room temperature. Butylamine (0.20 ml, 2.0 mmol) was added dropwise over 30 min and stirring was continued for 18 hr at room temperature. Hydrochloric acid (15 ml, 0.4 N) was warmed to 60° C., added to the mixture and stirring was continued for 1 hr. The resulting mixture was extracted into ethyl acetate, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a solid. The crude solid was triturated with methanol to give 0.90 g (33%) of a yellow solid: mp 140-142° C. [expected mp 139-140° C.]; 1H NMR: δ 5.84 (s, 1H), 6.62 (d, 2H, J=15.7 Hz), 7.39 (m, 6H), 7.54 (dd, 4H, J=7.4, 4.0 Hz), 7.66 (d, 2H, J=15.9 Hz), 15.85 (s, 1H); 13C NMR: δ 101.6, 124.1, 128.0, 128.9, 130.0, 135.0, 140.5, 183.2.

출처