Isobutyl nitrite → 2-Oximino-4-methyl-5-ethyltetrahydro-1,4-oxazin-3-one
Reaction equation
CC(C)([O-])C.[K+].[CH3:7][N:8]1[CH:13]([CH2:14][CH3:15])[CH2:12][O:11][CH2:10][C:9]1=[O:16].[N:17](OCC(C)C)=[O:18]>O1CCCC1>[N:17](=[C:10]1[C:9](=[O:16])[N:8]([CH3:7])[CH:13]([CH2:14][CH3:15])[CH2:12][O:11]1)[OH:18]Participants
Procedure
A quantity of 33.7 g of potassium t-butoxide, 40.0 g of 4-methyl-5-ethyl-tetrahydro-1,4-oxazin-3-one, and 29.3 g of isobutyl nitrite were caused to react sequentially in 800 ml of anhydrous tetrahydrofuran in a manner similar to that described in Example III. Following a similar workup, 44.7 g of a thick oil were obtained which could not be induced to crystallize. Part (10 grams) was chromatographed on silica gel eluting the product band (3.0 grams) with acetone after unchanged starting material (5.4 grams) had been eluted with isopropyl ether/acetone mixtures. Trituration of the product fraction with ethyl acetate afforded pure oxime product, 2.9 g, mp. 168.5°-170.0°, equivalent to a total yield (in 44.7 g of crude product) of 13.0 grams.
Sources & evidence
- ORD record
- ord-df5258988eee483bb0b62fa1c5992032
- Source dataset
- uspto-grants-1980_11
- Patent number
- US04235902
Reaction notes
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