Iodoethane → HCID 19002980, compound

HRID 2259233Notes

Reaction equation

HRID 2259233 reaction equation
[CH2:1]([O:8][CH2:9][N:10]1[C:14]([S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:13]([CH2:22][CH3:23])[N:12]=[CH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:24]([Li])[CH2:25]CC.CCCCCC.C(I)C>O1CCCC1.CN(C)P(=O)(N(C)C)N(C)C>[CH2:1]([O:8][CH2:9][N:10]1[C:14]([S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:13]([CH2:22][CH3:23])[N:12]=[C:11]1[CH2:24][CH3:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 8058HexaneHCID 475879HCID 475879, compoundHCID 178418339Butyllithium

Product 1

HCID 19002980HCID 19002980, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
-78 °C

Procedure

In a mixture of 5 ml of dry tetrahydrofuran and 2.5 ml of dry hexamethylphosphoric triamide is dissolved 150 mg of 1-benzyloxymethyl-4-ethyl-5-phenylthioimidazole (I-4) (0.46 mmol) obtained in Example 4, and the resulting solution is chilled at -78° C. To the solution is added dropwise 1.64M n-butyl lithium solution in 0.49 ml of hexane (0.8 mmol). Five minutes later, 110 mg of ethyl iodide (0.8 mmol) is added to the mixture, which mixture is allowed to stand for 10 minutes, when it is poured onto ice water and extracted with ethyl ether. The extract is washed with water, dried over sodium sulfate and filtered. The filtrate is chromatographed on a column of silica gel, eluting with ethyl acetate/n-hexane (1:2) to give 50 mg of the product (I-19) as an oil. Yield, 31%.

Workup

  1. customobtained in Example 4
  2. additionwhen it is poured onto ice water
  3. extractionextracted with ethyl ether
  4. washThe extract is washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customThe filtrate is chromatographed on a column of silica gel
  8. washeluting with ethyl acetate/n-hexane (1:2)

Sources & evidence

ORD record
ord-6ed6d79fdc474c6db58dfa81ce976a68
Source dataset
uspto-grants-1995_12
Patent number
US05472965

Reaction notes

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