Реакция #81082

Уравнение реакции

Trichloroacetonitrile

2-propen-1-ol

sodium hydride

→

title compound

2,2,2-Trichloroacetimidoic acid, 2-propenyl ester

Растворители

ether

ether

Условия реакции

Обработка

1. 1
   Промывкаwashed twice with 25 ml
2. 2
   Сушкаof hexane) in dry
3. 3
   workup.STIRRINGthe brownish solution was stirred at 0° C. for 40 minutes, at 10° C. for 10 minutes and at room temperature for 10 minutes
4. 4
   КонцентрированиеThe reaction mixture was concentrated to a syrup
5. 5
   workup.ADDITIONtreated with a solution of methanol (1.2 ml.) in pentane (30 ml.)
6. 6
   workup.STIRRINGstirred vigorously for 5.0 minutes
7. 7
   ДругоеThe light brown precipitates
8. 8
   Фильтрацияwere filtered off
9. 9
   Промывкаwashed with pentane (2×30 ml.)
10. 10
    Концентрированиеthe combined flitrates concentrated down to a light brown liquid
11. 11
    workup.DISSOLUTIONThe liquid was redissolved in pentane (30 ml.)
12. 12
    workup.STIRRINGstirred for a few minutes
13. 13
    Фильтрацияthe resulting suspension filtered
14. 14
    Другоеthe precipitates obtained
15. 15
    Промывкаwashed with pentane (30 ml.)
16. 16
    КонцентрированиеThe clear filtrate was concentrated
17. 17
    Другоеdried in vacuo
18. 18
    Другоеto give 54.0 g

Методика

A suspension of 80% sodium hydride (945 mg., 31.5 mmol.; washed twice with 25 ml. of hexane) in dry. ether (30 ml.) was treated dropwise with a solution of 2-propen-1-ol (21.4 ml., 18.3 g., 315 mmol.), in dry ether (45 ml.), stirred for 20 minutes at room temperature under argon and then cooled to 0° C. (ice-salt bath). Trichloroacetonitrile (30 ml. or 42.3 g., 0.30 mole) was added over a period of 15 minutes and the brownish solution was stirred at 0° C. for 40 minutes, at 10° C. for 10 minutes and at room temperature for 10 minutes. The reaction mixture was concentrated to a syrup, treated with a solution of methanol (1.2 ml.) in pentane (30 ml.) and stirred vigorously for 5.0 minutes. The light brown precipitates were filtered off, washed with pentane (2×30 ml.) and the combined flitrates concentrated down to a light brown liquid. The liquid was redissolved in pentane (30 ml.), stirred for a few minutes, and the resulting suspension filtered, and the precipitates obtained washed with pentane (30 ml.), repeating the procedure at least one more time. The clear filtrate was concentrated and dried in vacuo to give 54.0 g. of title compound as a light red-colored liquid. This material was stored as a solution in hexane at 10° C.

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