Sodium hydride → HCID 20476990, compound

HRID 905076Notes

Reaction equation

HRID 905076 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][SH:7])=[CH:4][CH:3]=1.[H-].[Na+].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:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][S:7][CH2:23][CH:24]2[CH2:29][CH2:28][CH:27]=[CH:26][O:25]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 804094-Chlorobenzyl mercaptanHCID 13071283(3,4-dihydro-2H-pyran-2-yl)methyl 4-methylbenzene-1-sulfonate

Product 1

HCID 20476990HCID 20476990, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 260 mg of 4-chlorobenzyl mercaptan in 3 ml of dimethylformamide was mixed with 72 mg of 55% sodium hydride, and the mixture was stirred at room temperature for 30 minutes. 2 ml of a dimethylformamide solution containing 400 mg of 2-tosyloxymethyl-3,4-dihydro-2H-pyran were then added, and the mixture was stirred at 80°-90° C. for 4 hours. The mixture was then treated and the product purified essentially as described in Example 34(a) to give 224 mg of 2-(4-chlorobenzylthiomethyl)-3,4-dihydro-2H-pyran, as a colourless oil.

Workup

  1. additionwere then added
  2. stirringthe mixture was stirred at 80°-90° C. for 4 hours
  3. additionThe mixture was then treated
  4. customthe product purified essentially

Sources & evidence

ORD record
ord-198b1b6a949b4c36824bba761cc609f8
Source dataset
uspto-grants-1983_12
Patent number
US04421758

Reaction notes

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