Methanol → HCID 20085210, compound

HRID 257729Notes

Reaction equation

HRID 257729 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH2:18][N:19]2[CH:23]=[N:22][CH:21]=[N:20]2)([CH2:14][CH2:15][CH2:16][CH3:17])[C:11]([OH:13])=[O:12])=[CH:6][CH:5]=1.[CH2:24](I)[CH3:25].CO>CN(C)C=O.C(OCC)(=O)C>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH2:18][N:19]2[CH:23]=[N:22][CH:21]=[N:20]2)([CH2:14][CH2:15][CH2:16][CH3:17])[C:11]([O:13][CH2:24][CH3:25])=[O:12])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 6340IodoethaneHCID 14798Sodium HydroxideHCID 15766659HCID 15766659, compound

Product 1

HCID 20085210HCID 20085210, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a 250 mL 3 neck flask stirring under N2 was charged 1.0 g of 60% sodium hydroxide (prewashed with hexanes) in 50 mL of dimethyl formamide (DMF). To the slurry was charged 6.14 g (0.020 mole) of 2-(4-chlorophenyl)-2-[(1,2,4-triazol-1-yl)methyl]hexanoic acid in 50 mL of dimethyl formamide. The mixture was stirred at room temperature and 3.74 g (0.024 mole) of ethyl iodide was added. The reaction was monitored by thin layer chromatography (TLC) in a one to 19 mixture of methanol and ethyl acetate. Upon completion the reaction was quenched with water extracted with ether, and washed with saturated sodium bicarbonate. After drying and removal of the solvent, 5.9 g (88% yield) of a thick oil remained, Example 18 of Table 1.

Workup

  1. customUpon completion the reaction was quenched with water
  2. extractionextracted with ether
  3. washwashed with saturated sodium bicarbonate
  4. customAfter drying

Sources & evidence

ORD record
ord-2ce614e8026c46f98350370902230951
Source dataset
uspto-grants-1993_11
Patent number
US05264415

Reaction notes

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