Triethylamine → HCID 73986571, compound

HRID 840088Notes

Reaction equation

HRID 840088 reaction equation
[C:1]1([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10](=O)[CH3:11])[CH2:3][CH:2]=1.C(N(CC)CC)C.Cl.[O:21]([NH2:23])[CH3:22]>CO>[CH3:22][O:21][N:23]=[C:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:1]1[CH2:3][CH:2]=1)[CH3:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 22621693HCID 22621693, compound

Product 1

HCID 73986571HCID 73986571, compoundYield 28.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.15 g (0.9 mmol) of 8-cycloprop-1-enyl-octan-2-one in 10 mL of methanol cooled in an ice bath was added 0.30 g (3 mmol1) of triethylamine and 0.83 g of a 30-35% aqueous solution of methoxylamine hydrochloride (3 mmol). The ice bath was removed, and the reaction mixture was stirred at room temperature for 1.5 hours. Water and ether were added. The phases were separated and the aqueous phase was washed with ether. The combined ether phases were washed with dilute aqueous hydrochloride acid, water (2×), and brine, then dried over magnesium sulfate, filtered and stripped. Column chromatography gave 50 mg of 8-cycloprop-1-enyl-octan-2-one O-methyl oxime (Compound 47) as a 30% solution in ether. The ratio of oxime isomers was 3:1.

Workup

  1. customThe ice bath was removed
  2. additionWater and ether were added
  3. customThe phases were separated
  4. washthe aqueous phase was washed with ether
  5. washThe combined ether phases were washed with dilute aqueous hydrochloride acid, water (2×), and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered

Sources & evidence

ORD record
ord-c29a07f7776748e5a0fb3face1ab23c0
Source dataset
uspto-grants-2002_04
Patent number
US06365549B2

Reaction notes

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