Hydrochloric Acid → HCID 21317568, compound

HRID 328800Notes

Reaction equation

HRID 328800 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:21])[CH:6]([S:17]([CH3:20])(=[O:19])=[O:18])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14].[H][H].I[CH2:25][CH2:26][CH2:27][CH:28]([O:41][C:42](=[O:44])[CH3:43])[CH2:29][O:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[CH:32]=1.Cl>CN(C)C=O.O.CCOCC>[CH3:20][S:17]([C:6]([C:5]([O:4][CH3:3])=[O:21])([CH2:25][CH2:26][CH2:27][CH:28]([O:41][C:42](=[O:44])[CH3:43])[CH2:29][O:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:39])([F:40])[F:38])[CH:32]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])(=[O:19])=[O:18]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 21317577HCID 21317577, compoundHCID 54054723Dimethyl-2-methylsulfonylazelateHCID 178418361HCID 178418361, compound

Product 1

HCID 21317568HCID 21317568, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent3×

Conditions

Temperature
5 °C

Procedure

A 50% oil dispersion of sodium hydride (2.11 g., 0.044 mole) in mineral oil is washed with petroleum ether and then suspended in dry dimethylformamide (30 ml.) under a nitrogen atmosphere at room temperature. To this suspension is added a solution of dimethyl-2-methylsulfonyl-azelate (11.8 g., 0.04 mole) in dry dimethylformamide (30 ml.). After the evolution of hydrogen is completed, the mixture is cooled to 5° C. in an ice bath and a solution of 1-iodo-4-acetoxy-5-(3-trifluoromethylphenoxy)pentane (18.3 g., 0.044 mole) in dry dimethylformamide (30 ml.) is added dropwise. After 48 hours, ether is added to the reaction mixture to precipitate sodium iodide which is removed by filtration. The filtrate is concentrated in vacuo to give a residue which is diluted with water, acidified with 6N hydrochloric acid, and extracted with ether. The ether extracts are washed with water until neutral, dried over anhydrous magensium sulfate, and concentrated in vacuo to give the title compound (20.5 g., 0.035 mole, 88%).

Workup

  1. customto precipitate sodium iodide which
  2. customis removed by filtration
  3. concentrationThe filtrate is concentrated in vacuo
  4. customto give a residue which
  5. extractionextracted with ether
  6. washThe ether extracts are washed with water until neutral,
  7. dry with materialdried over anhydrous magensium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-02865890d17948a892b135542e046d54
Source dataset
uspto-grants-1977_04
Patent number
US04018802

Reaction notes

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