Water → HCID 13071286, compound

HRID 905087Notes

Reaction equation

HRID 905087 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[H-].[Na+].S(O[CH2:25][CH:26]1[CH2:31][CH2:30][CH:29]=[CH:28][O:27]1)(C1C=CC(C)=CC=1)(=O)=O.O>CN(C)C=O>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:25][CH:26]2[CH2:31][CH2:30][CH:29]=[CH:28][O:27]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 1983AcetaminophenHCID 24758Sodium hydrideHCID 13071283(3,4-dihydro-2H-pyran-2-yl)methyl 4-methylbenzene-1-sulfonate

Product 1

HCID 13071286HCID 13071286, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 831 mg of 4-acetamidophenol in 5 ml of dimethylformamide was stirred for 30 minutes at room temperature with 240 mg of 55% sodium hydride. 1.34 g of 2-tosyloxymethyl-3,4-dihydro-2H-pyran was then added and the mixture was heated, with stirring, at 90°-95° C. for 4.5 hours. The mixture was then poured into water and extracted with diethyl ether. The ethereal extract was washed with water and dried over anhydrous magnesium sulphate, after which the solvent was evaporated off. The residue was purified by column chromatography through silica gel, to give 965 mg of the title compound, melting at 114°-116° C.

Workup

  1. temperaturethe mixture was heated
  2. extractionextracted with diethyl ether
  3. extractionThe ethereal extract
  4. washwas washed with water
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customafter which the solvent was evaporated off
  7. customThe residue was purified by column chromatography through silica gel

Sources & evidence

ORD record
ord-34eb2385b3164b2e9dc261204050e757
Source dataset
uspto-grants-1983_12
Patent number
US04421758

Reaction notes

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