Sodium hydride → HCID 66704071, compound

HRID 424843Notes

Reaction equation

HRID 424843 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10]P(OCC)(OCC)=O)[CH:5]=1.[H-].[Na+].[Cl:22][C:23]1[CH:30]=[C:29]([O:31][CH2:32][C:33]2[N:34]([C:41]3[C:46]([Cl:47])=[CH:45][CH:44]=[CH:43][C:42]=3[Cl:48])[N:35]=[N:36][C:37]=2[CH:38]([CH3:40])[CH3:39])[CH:28]=[CH:27][C:24]=1[CH:25]=O>C(OCC)C>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]=[CH:25][C:24]2[CH:27]=[CH:28][C:29]([O:31][CH2:32][C:33]3[N:34]([C:41]4[C:42]([Cl:48])=[CH:43][CH:44]=[CH:45][C:46]=4[Cl:47])[N:35]=[N:36][C:37]=3[CH:38]([CH3:40])[CH3:39])=[CH:30][C:23]=2[Cl:22])[CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 54175643HCID 54175643, compoundHCID 86629255HCID 86629255, compound

Product 1

HCID 66704071HCID 66704071, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a 0° C. solution of 3-(diethoxy-phosphorylmethyl)-benzoic acid methyl ester (1.2 g, 4 eq) in diethyl ether (15 mL) is added sodium hydride (0.17 g, 4 eq). After 1 h, 2-chloro-4-[3-(2,6-dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-benzaldehyde (0.44 g, 1 eq) in diethyl ether (5 mL) is added and the reaction is stirred overnight. Upon completion, the reaction is quenched with water. The aqueous solution is acidified with 1N HCl and extracted two times with ethyl acetate. The organic layers are combined, washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue is purified via filter chromatography eluting with 10% ethyl acetate:toluene to give 3-(2-{2-Chloro-4-[3-(2,6-dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-phenyl}-vinyl)-benzoic acid methyl ester (0.459 g).

Workup

  1. customUpon completion, the reaction is quenched with water
  2. extractionextracted two times with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified
  8. filtrationvia filter chromatography
  9. washeluting with 10% ethyl acetate

Sources & evidence

ORD record
ord-595b80f05104476d8349aa3cfea6a28f
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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