Water → HCID 19955537, compound

HRID 440952Notes

Reaction equation

HRID 440952 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)(=O)=O.[I-:21].[Na+].O>CC(C)=O>[C:11]1([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][I:21])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5238Sodium IodideHCID 19955547HCID 19955547, compound

Product 1

HCID 19955537HCID 19955537, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Under a nitrogen atmosphere, a stirred solution of 4.1 grams (0.014 mole) of 1-methylsulfonyloxy-5-(naphth-1-yl)pentane, and 4.2 grams (0.028 mole) of sodium iodide in 150 mL of acetone was heated at reflux for 2.5 hours. The reaction mixture was poured into 400 mL of water, and the mixture was extracted with two 100 mL portions of diethyl ether. The combined extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 3.9 grams of 5-(naphth-1-yl)pentyl iodide. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureat reflux for 2.5 hours
  2. extractionthe mixture was extracted with two 100 mL portions of diethyl ether
  3. dry with materialThe combined extracts were dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2321a450ca124ea68b730f2a0cda5e26
Source dataset
uspto-grants-1996_05
Patent number
US05521192

Reaction notes

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