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

HRID 2451
Notes
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Reaction equation

HRID 2451 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

HCID 538179164-Tetrahydropyranyloxymethyl-N-(2-methoxyphenyl)benzenesulfonamideYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-22c3de4c1b024e1b99af0b155d809e56
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05728835

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes