4-Chlorobenzyl alcohol → 2-(4-chlorobenzyloxymethyl)-3,4-dihydro-2H-pyran

HRID 905073Notes

Reaction equation

HRID 905073 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1.S(O[CH2:23][CH:24]1[CH2:29][CH2:28][CH:27]=[CH:26][O:25]1)(C1C=CC(C)=CC=1)(=O)=O>CN(C)C=O>[Cl:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][O:9][CH2:23][CH:24]2[CH2:29][CH2:28][CH:27]=[CH:26][O:25]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 133974-Chlorobenzyl alcoholHCID 24758Sodium hydrideHCID 13071283(3,4-dihydro-2H-pyran-2-yl)methyl 4-methylbenzene-1-sulfonate

Product 1

HCID 204769372-(4-chlorobenzyloxymethyl)-3,4-dihydro-2H-pyranYield 28.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

50 mg of 55% sodium hydride were added to a solution of 193 mg of 4-chlorobenzyl alcohol in 1 ml of dimethylformamide, and the mixture was stirred at room temperature for 30 minutes. A solution of 326 mg of 2-tosyloxymethyl-3,4-dihydro-2H-pyran in 2 ml of dimethylformamide was then added and the resulting mixture was allowed to react at 90° C. for 4 hours. The mixture was then treated and the product purified essentially as described in Example 34(a), to give 82 mg of 2-(4-chlorobenzyloxymethyl)-3,4-dihydro-2H-pyran, as a colourless oil.

Workup

  1. customto react at 90° C. for 4 hours
  2. additionThe mixture was then treated
  3. customthe product purified essentially

Sources & evidence

ORD record
ord-ff1bc684e6d240ddae6d8d3ce15fa46e
Source dataset
uspto-grants-1983_12
Patent number
US04421758

Reaction notes

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