Aldoxime → HCID 67814333, compound

HRID 589098Notes

Reaction equation

HRID 589098 reaction equation
[C:1]([O:9][CH2:10][C:11]#[CH:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:20](=[N:22][OH:23])[CH3:21].Cl[O-].[Na+]>C(Cl)(Cl)Cl>[C:1]([O:9][CH2:10][C:11]1[O:23][N:22]=[C:20]([CH3:21])[CH:12]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7863AldoximeHCID 8471TriethylamineHCID 336291Prop-2-yn-1-yl benzoateHCID 23665760Sodium Hypochlorite

Product 1

HCID 67814333HCID 67814333, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

A solution of prop-2-yn-1-yl benzoate (26.0 g, 162 mmol) in chloroform (598 mL) was treated with triethylamine (11.3 mL, 81.2 mmol) and acetaldoxime (14.4 g, 244 mmol). The reaction mixture was cooled to 0° C., treated with sodium hypochlorite (551 mL, 487 mmol) (commercial grade ˜5% aqueous), and stirred overnight at room temperature. The layers were separated and the aqueous layer was extracted with dichloromethane (2×200 mL). The combined organic layers were washed with water and brine, dried over magnesium sulfate, filtered, and concentrated to give the crude product. Purification by flash column chromatography (100% hexanes to 30% ethyl acetate/hexanes) gave the desired product (20.1 g, 57%). LCMS calculated for C12H12NO3 (M+H)+: m/z=218.1. found: 218.1.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with dichloromethane (2×200 mL)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product
  8. customPurification by flash column chromatography (100% hexanes to 30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-84a3894083a5454bb93f5d847aef7a1e
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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