Реакция #1052615

Уравнение реакции

dioxetane

4-(2,2,2-Trifluoroethoxy)-4-(3-hydroxyphenyl)spiro[1,2-dioxetane-3,2'-tricyclo[3.3.1.13,7 ]decane]

pyridine

acetyl chloride

→

oil

4-(2,2,2-Trifluoroethoxy)-4-(3-acetoxyphenyl)spiro[1,2-dioxetane-3,2'-tricyclo[3.3.1.13,7 ]decane]

Растворители

CH2Cl2

Условия реакции

Обработка

1. 1
   Температураwas heated
2. 2
   ДругоеThe volatiles were removed in vacuo
3. 3
   Другоеleaving a yellow oil which
4. 4
   Другоеwas purified by preparative TLC

Методика

A solution of dioxetane 3 (78.2 mg) in 15 mL of CH2Cl2 was placed under argon. Dry pyridine (40 μL, 2.3 eq.) was added followed after 5 min by 16.6 μL (1.1 eq.) of acetyl chloride. The reaction was judged complete by TLC after 2 hours, showing a new material which emitted blue-green light when the plate was heated. The volatiles were removed in vacuo leaving a yellow oil which was purified by preparative TLC using CH2Cl2 as eluent. A colorless oil (44 mg) was obtained: 1H NMR (CDCl3) δ 0.98 (m, 1H), 1.29 (m, 1H), 1.46-2.00 (m, 10H), 2.20 (br s, 1H), 2.325 (s, 3H), 3.06 (br s, 1H), 3.624 (dq, 1H), 3.938 (dq, 1H), 7.20 (dd, 1H), 7.28-7.64 (m, 3H).

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