4-Toluenesulfonyl chloride → 2-Methoxyethyl alpha-(4-methylphenylsulfonyloxyimino)-2-phenylacetate

HRID 393136Notes

Reaction equation

HRID 393136 reaction equation
[OH:1][N:2]=[C:3]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:4]([O:6][CH2:7][CH2:8][O:9][CH3:10])=[O:5].C(N(CC)CC)C.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1>O1CCCC1>[CH3:34][C:24]1[CH:29]=[CH:28][C:27]([S:30]([O:1][N:2]=[C:3]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:4]([O:6][CH2:7][CH2:8][O:9][CH3:10])=[O:5])(=[O:32])=[O:31])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 739911462-Methoxyethyl alpha-(hydroxyimino)-2-phenylacetate

Product 1

HCID 539744012-Methoxyethyl alpha-(4-methylphenylsulfonyloxyimino)-2-phenylacetateYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 8.8 g (0.39 mol) of crude 2-methoxyethyl α-(hydroxyimino)-2-phenylacetate and 5.98 g of triethylamine in 65 ml tetrahydrofuran is cooled in an ice bath, and 8.3 g (0.043 mol) of p-toluenesulfonic acid chloride dissolved in 18 ml of tetrahydrofuran are added dropwise over 30 minutes. The resulting suspension is stirred for 16 hours at room temperature and then poured onto ice/water. The mixture is extracted with ethyl acetate, the organic layer washed with diluted HCI and water and dried over magnesium sulfate. Evaporation of the solvent gives an orange oil which is purified by chromatography on silica gel (eluent hexane/ethyl acetate 3:1). 12.68 g (86%) 2-Methoxyethyl α-(4-methylphenylsulfonyloxyimino)-2-phenylacetate are thus obtained as a colorless liquid. According to 1H-NMR-analysis, the product is a mixture of 72% of the trans isomer and 28% of the cis isomer.

Workup

  1. additionare added dropwise over 30 minutes
  2. additionpoured onto ice/water
  3. extractionThe mixture is extracted with ethyl acetate
  4. washthe organic layer washed with diluted HCI and water
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent
  7. customgives an orange oil which
  8. customis purified by chromatography on silica gel (eluent hexane/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-bbbc3a2a85bb4cc4a9a21a1b1466753f
Source dataset
uspto-grants-2004_10
Patent number
US06806024B1

Reaction notes

Loading…