반응 #81082

반응 방정식

Trichloroacetonitrile

2-propen-1-ol

sodium hydride

→

title compound

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

용매

ether

ether

반응 조건

후처리

1. 1
   세척washed twice with 25 ml
2. 2
   건조of 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
   농축The 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
   기타The light brown precipitates
8. 8
   여과were filtered off
9. 9
   세척washed with pentane (2×30 ml.)
10. 10
    농축the 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
    여과the resulting suspension filtered
14. 14
    기타the precipitates obtained
15. 15
    세척washed with pentane (30 ml.)
16. 16
    농축The clear filtrate was concentrated
17. 17
    기타dried in vacuo
18. 18
    기타to give 54.0 g

실험 절차

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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