Iodoethane → HCID 20164627, compound

HRID 255841Notes

Reaction equation

HRID 255841 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH3:20])[C:10]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)([OH:13])[CH2:11][OH:12].[H-].[Na+].[CH2:23](I)[CH3:24].C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH2:23]([O:12][CH2:11][C:10]([CH:9]([CH3:20])[C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1])([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[OH:13])[CH3:24]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 20164694HCID 20164694, compound

Product 1

HCID 20164627HCID 20164627, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.2 g of 3-(2,4-dichlorophenyl)-2-(3-pyridyl)-1,2-butanediol are dissolved under argon in 19 ml of N,N-dimethylformamide and treated at -15° C. with 0.12 g of sodium hydride (99%). The mixture is left to come to 0° C. and stirred at this temperature for 6 hours and 0.4 ml of ethyl iodide is added thereto. There thereby results a red-orange colored suspension which, after stirring at 0° C. for 1 hour, is treated with 20 ml of saturated aqueous sodium bicarbonate solution and subsequently evaporated under a pressure of 0.1 mmHg in order to remove the solvent. The residue is taken up in water and the aqueous solution extracted with ethyl acetate, and the organic phase is washed with saturated aqueous sodium chloride solution and then evaporated to dryness under reduced pressure. The oily residue is purified by chromatography on silica gel with diethyl ether/n-hexane (17:3) and it is recrystallized from methylene chloride/n-hexane. In this manner there is obtained 0.7 g of α-ethoxymethyl-α-(2,4-dichloro-α-methylbenzyl)-3-pyridinemethanol as colorless crystals, m.p. 86° C.

Workup

  1. waitThe mixture is left
  2. customto come to 0° C.
  3. customThere thereby results a red-orange colored suspension which
  4. stirringafter stirring at 0° C. for 1 hour
  5. customsubsequently evaporated under a pressure of 0.1 mmHg in order
  6. customto remove the solvent
  7. extractionthe aqueous solution extracted with ethyl acetate
  8. washthe organic phase is washed with saturated aqueous sodium chloride solution
  9. customevaporated to dryness under reduced pressure
  10. customThe oily residue is purified by chromatography on silica gel with diethyl ether/n-hexane (17:3) and it
  11. customis recrystallized from methylene chloride/n-hexane

Sources & evidence

ORD record
ord-5f867b6d53364aeda3c5119c89620933
Source dataset
uspto-grants-1987_10
Patent number
US04699652

Reaction notes

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