Allyl Alcohol → Allyl 2,2,2-Trichloroacetimidate

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 minut 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 filtrates 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.

1. washwashed twice with 25 ml
2. stirringthe brownish solution was stirred at 0° C. for 40 minutes, at 10° C. for 10 minutes and at room temperature for 10 minutes
3. concentrationThe reaction mixture was concentrated to a syrup
4. additiontreated with a solution of methanol (1.2 ml.) in pentane (30 ml.)
5. stirringstirred vigorously for 5.0 minutes
6. customThe light brown precipitates
7. filtrationwere filtered off
8. washwashed with pentane (2×30 ml.)
9. concentrationthe combined filtrates concentrated down to a light brown liquid
10. dissolutionThe liquid was redissolved in pentane (30 ml.)
11. stirringstirred for a few minutes
12. filtrationthe resulting suspension filtered
13. customthe precipitates obtained
14. washwashed with pentane (30 ml.)
15. concentrationThe clear filtrate was concentrated
16. customdried in vacuo
17. customto give 54.0 g

ORD record

ord-4aee3d96e0b24d9e918e240f3b49de85

Source dataset

uspto-grants-1998_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05756832