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

HRID 393136ノート

反応式

HRID 393136 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-bbbc3a2a85bb4cc4a9a21a1b1466753f
出典データセット
uspto-grants-2004_10
特許番号
US06806024B1

反応ノート

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