Sodium hydride → HCID 14878964, compound

HRID 2371469Notes

Reaction equation

HRID 2371469 reaction equation
[H-].[Na+].Cl[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:6]=1.[Cl:18][CH2:19][C:20]([CH3:24])([CH3:23])[CH2:21][OH:22]>CN(C=O)C>[Cl:18][CH2:19][C:20]([CH3:24])([CH3:23])[CH2:21][O:22][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 834071-Propanol, 3-chloro-2,2-dimethyl-HCID 138492412-Chloromethyl-6-phenoxypyridine

Product 1

HCID 14878964HCID 14878964, compoundYield 11.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under a nitrogen atmosphere, 0.65 g of sodium hydride (60% oily suspension) was suspended in 10 ml of dry DMF, and a solution of 3.23 g of 2-chloromethyl-6-phenoxypyridine and 2.00 g of 3-chloro-2,2-dimethylpropanol in 10 ml of dry DMF was added dropwise with ice-cooling. After stirring for 12 hours at room temperature, the reaction solution was poured into dilute hydrochloric acid-ice water and extracted twice with diethyl ether. The ether layers were combined, washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was subjected to column chromatography on silica gel (developing solvent, hexane:ethyl acetate=50:1) to obtain 0.52 g of desired 6-phenoxy-2-pyridylmethyl 3-chloro-2,2-dimethylpropyl ether [present compound (1)] as a colorless oily product.

Workup

  1. temperaturecooling
  2. extractionextracted twice with diethyl ether
  3. washwashed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-af0a3eec97c943dd923387a345627617
Source dataset
uspto-grants-1992_03
Patent number
US05093373

Reaction notes

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