3,4-dihydro-2H-pyran → 4-Tetrahydropyranyloxymethyl-N-(2-methoxyphenyl)benzenesulfonamide

HRID 2451

反応式

HRID 2451 の反応式
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH3:20])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[O:21]1[CH:26]=[CH:25][CH2:24][CH2:23][CH2:22]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[O:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]1[O:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH3:20])(=[O:10])=[O:11])=[CH:7][CH:8]=1

参加物

6

反応物 4

HCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 196899084-Hydroxymethyl-N-(2-methoxyphenyl)benzenesulfonamide

生成物 1

HCID 538179164-Tetrahydropyranyloxymethyl-N-(2-methoxyphenyl)benzenesulfonamide収率 91.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

4-Hydroxymethyl-N-(2-methoxyphenyl)benzenesulfonamide (99.6 mg, 0.34 mmol) was dissolved in methylene chloride (3 ml) to which, with cooling in an ice bath, were subsequently added 3,4-dihydro-2H-pyrane (48 μl, 0.51 mmol) and a catalytically effective amount of p-toluenesulfonic acid monohydrate. After 90 minutes of stirring at the same temperature, the reaction solution was mixed with saturated sodium bicarbonate aqueous solution (5 ml) and extracted with ether. The resulting organic layer was washed with saturated brine and dried on anhydrous magnesium sulfate, and the solvent was removed by evaporation. Thereafter, the thus obtained light yellow oily material was purified by a silica gel column chromatography (ether:hexane=1:1) to obtain 117 mg (91.2%) of the title compound in the form of colorless solid.

後処理

  1. temperaturewith cooling in an ice bath
  2. extractionextracted with ether
  3. washThe resulting organic layer was washed with saturated brine
  4. dry with materialdried on anhydrous magnesium sulfate
  5. customthe solvent was removed by evaporation
  6. customThereafter, the thus obtained light yellow oily material was purified by a silica gel column chromatography (ether:hexane=1:1)

出典と根拠

ORDレコード
ord-22c3de4c1b024e1b99af0b155d809e56
出典データセット
uspto-grants-1998_03
特許番号
US05728835

関連ノート

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