O-[(2E)-3-Chloro-2-propen-1-yl]hydroxylamine

the step (3) was obtained 2- (3-chloro-allyloxy) indolizine isobutyl-1, 3-dione was added 35percent hydrochloric acid hydrolysis, the hydrolysis is completed, filtration, liquid separation to collect the organic phase, i.e., the product of 3-chloro-2-propenyl-O-yl yield 46.6 g of hydroxylamine, a total yield of 72.0percent, content 98.3percent.Trans-2-[1-(3-chloroallyloxyamino)-ethylidene]-5-(2-ethylthiopropyl)-cyclohexane-1, 3-dione In this example, 29.5 g (0.1151 mol) of 2-acetyl-5-(2-ethylthiopropyl)cyclohexane-1, 3-dione; 1.7 g (0.0277 mol) of acetic acid, and 19.7 g (0.1369 mol) of 2-[1-(3-chloroallyloxyimino)propyl]-3-hydroxy-5-(4-methanesulfonamidophenyl)-2-cyclohexen-1-one Into 40 ml of mixture solvent of ethanol-chloroform (1:1) was dissolved 2 g of 3-hydroxy-5-(4-methanesulfonamidophenyl)-2-propionyl-2-cyclohexen-1-one and to the solution was added 10 ml of ethanol containing 10percent of EXAMPLE 4 Preparation of (E)-2-[1-(3-chloro-2-propenyloxyimino)propyl]-5-(1, 3-dimethyl-1H-pyrazol-5-yl)cyclohexane-1, 3-dione (Compound No. 4) STR19 To 10 ml of a solution of 5.60 g (21.3 mmols) of 5-(1, 3-dimethyl-1H-pyrazol-5-yl)-2-propionylcyclohexane-1, 3-dione in methanol was added 57 ml (21.7 mmols) of 0.38 mol ethanolic solution of 2. Preparation of (E)-2-[1-(3-chloro-2-propenyloxyimino)propyl]5-(1-methyl-1H-pyrazol-4-yl)cyclohexane-1, 3-dione (Compound No. 1) STR15 To 200 ml of an ethanolic solution of 20.0 g (81 mmols) of 5-(1-methyl-1H-pyrazol-4-yl)-2-propionylcyclohexane-1, 3-dione was added 210 ml (84 mmols) of 0.4 mol ethanolic solution of Preparation of (E)-2-[1-(3-chloro-2-propenyloxyimino) propyl]-5-(1-methyl-1H-pyrazol-5-yl)-cyclohexane-1, 3-dione (Compound No. 2) STR16 To 5 ml of an ethanolic solution of 0.35 g (1.4 mmols) of 5-(1-methyl-1H-pyrazol-5-yl)-2-propionylcyclohexane-1, 3-dione was added 3.8 ml (1.4 mmols) of 0.38 mol ethanolic solution of d) 2-(1-((E)-3-Chloro-2-propenyloxyimino)propyl)-5-(3, 7-dioxabicyclo[4.1.0]hept-6-yl)-3-hydroxycyclohex-2-enone 7.9 g (29.5 mmol) of 2-(1-oxopropyl)-5-(3, 7-dioxabicyclo[4.1.0]-hept-6-yl)-3-hydroxycyclohex-2-enone in 20 ml of methanol were mixed at room temperature with 3.5 g (32.4 mmol) of g) Clethodim Synthesis The formula VIII trione intermediate and O-(3-Chloro-2-propenyl)hydroxylamine (CPHA) (ca. equal molar amounts) are reacted in a mixed hexanes-water system that has been adjusted to pH 5.5-6.0, with sodium hydroxide, and buffered by addition of acetic acid. The exotherm (ca. 5-10 C.) is permitted to proceed unchecked. The reaction mixture is then stirred overnight at ambient temperature. Reaction completion is verified by HPLC analysis. The aqueous layer is separated and discarded. To the organic layer is added water and then sodium hydroxide to pH 12-14. The organic layer is separated and discarded. To the aqueous layer is added hexanes and then concentrated hydrochloric acid to obtain an acidic pH. The aqueous layer is separated and discarded. The organic layer is washed with water and then dried over sodium sulfate and stripped to yield an amber oil. Analysis of the resulting (-)-enantiomer includes verification of generic identity by NMR analysis and determination of chiral identity by specific rotation and separation under chiral HPLC conditions to determine enantiomeric excesses. Equal and opposite specific rotations [alpha]D24=28 (C=ca. 6×10-3 M in methanol) are determined on a polarimeter.The cyclohexanone derivatization method is described immediately below. Weigh about 2.00 g of sample in a vial containing 2.20 g of cyclohexanone; Add 50percent sodium hydroxide if necessary to bring pH to above 9. Stir the mixture in the capped vial at 50° C. for 2 hours. After cooling, add 8.0 g of dichloromethane and shake for one minute. Settle the mixture for 5 minutes. Take the organic phase for gas chromatographic (GC) analysis. CPHA purity and impurity profile are directly based on GC area. Hydroxylamine content is calculated based on the integration area of cyclohexanone oxime (cyclohexanoxime) peak and O-(chloro-2-propenyl)cyclohexanoxime peak.

Molecular Weight:107.54
XLogP3:0.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:107.0137915
Monoisotopic Mass:107.0137915
Topological Polar Surface Area:35.2
Heavy Atom Count:6
Complexity:46.1
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes