반응 #1682240

반응 방정식

Alkene

2,2-Diisopropyl-1-(3-hydroxyphenyl)-1-methoxyethene

Pivaloyl chloride

→

1-(3-Pivaloyloxyphenyl)-2,2-diisopropyl-1-methoxyethene

용매

CH2Cl2

triethylamine

반응 조건

후처리

1. 1
   기타The flask was purged with argon
2. 2
   온도cooled in an ice bath
3. 3
   기타The cooling bath was removed
4. 4
   세척The solution was washed with aq. K2CO3
5. 5
   건조water, dried over MgSO4
6. 6
   기타evaporated
7. 7
   기타The residue was purified by column chromatography on silica gel
8. 8
   세척eluting with 5% triethylamine in hexane yielding 1.95 g of dioxetane 1e

실험 절차

Alkene 1b (2 g, 8.6 mmol) was dissolved in 50 mL of dry CH2Cl2 with 2.4 mL of anhydrous triethylamine. The flask was purged with argon and cooled in an ice bath. Pivaloyl chloride (1.6 g, 2 eq.) was added dropwise over one hour. The cooling bath was removed and stirring continued for 3 hours at room temperature. The solution was washed with aq. K2CO3 and then water, dried over MgSO4 and evaporated. The residue was purified by column chromatography on silica gel, eluting with 5% triethylamine in hexane yielding 1.95 g of dioxetane 1e: 1H NMR (CDCl3) δ 7.34-6.98 (m, 4H), 3.198 (s, 3H), 2.47 (sept, 1H), 2.33 (sept, 1H), 1.36 (s, 9H), 1.24 (d, 6H, J=6.9 Hz), 0.92 (d, 6H, J=6.9 Hz).

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