Sodium Iodide → HCID 54388384, compound

HRID 905064Notes

Reaction equation

HRID 905064 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[H-].[Na+].[I-].[Na+].[Cl:10][C:11]1[CH:45]=[C:44]([Cl:46])[CH:43]=[CH:42][C:12]=1[CH2:13][CH:14]([O:23][C@@H:24]1[O:29][C@@H:28]([CH2:30]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:27][CH2:26][CH2:25]1)[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1>CN(C)C=O>[Cl:10][C:11]1[CH:45]=[C:44]([Cl:46])[CH:43]=[CH:42][C:12]=1[CH2:13][CH:14]([O:23][C@@H:24]1[O:29][C@@H:28]([CH2:30][N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)[CH2:27][CH2:26][CH2:25]1)[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 54166113HCID 54166113, compound

Product 1

HCID 54388384HCID 54388384, compoundYield 11.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

97.5 mg of 1,2,4-triazole and 62 mg of 55% sodium hydride, 142 mg of sodium iodide, 533 mg of trans-6-[α-(2,4-dichlorobenzyl)-4-methoxybenzyloxy]-2-tosyloxymethyltetrahydropyran and 6 ml of dimethylformamide were reacted and treated essentially as described in Example 3(b) and then the product was purified by column chromatography through silica gel eluted with a 1:2 by volume mixture of benzene and ethyl acetate, to give 244 mg of an isomer of lesser polarity, 109 mg of an isomer of greater polarity and 52 mg of a mixture of the two isomers (in which the ratio of the isomers of lesser to greater polarity was about 2:1).

Workup

  1. additiontreated essentially
  2. customthe product was purified by column chromatography through silica gel
  3. washeluted with a 1:2 by volume mixture of benzene and ethyl acetate

Sources & evidence

ORD record
ord-4017fdfce22d449d83f4409d512b8c12
Source dataset
uspto-grants-1983_12
Patent number
US04421758

Reaction notes

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