Methyl iodide → HCID 54328782, compound

HRID 1886383Notes

Reaction equation

HRID 1886383 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][O:7][N:8]=[C:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]2[C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:4][CH:3]=1.C([Li])CCC.CCCCCC.[C:34](=[S:36])=[S:35].[CH3:37]I>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][O:7][N:8]=[C:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]2([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[C:34]([S:36][CH3:37])=[S:35])=[CH:21][CH:22]=1

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8058HexaneHCID 539344632-(3-Pyridinyl)cyclohexanone O-[(4-fluorophenyl)methyl]oximeHCID 178418339Butyllithium

Product 1

HCID 54328782HCID 54328782, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
20 °C

Procedure

A stirred solution of 2-(4-fluorobenzyloxyimino) -1-pyrid-3-ylcyclohexane (150 mg, 0.5 mmol) in tetrahydrofuran (2 ml) at -78° C. was treated with 1.5M butyl lithium in hexane (0.44 ml, 0.65 mmol) over 5 minutes. After 30 minutes at -78° C. the solution was treated with carbon disulphide (57 mg, 0.75 mmol) in tetrahydrofuran (0.5 ml). The temperature of the reaction mixture was then allowed to rise, over 30 minutes to 0° C., and was then treated with a solution of methyl iodide (107 mg, 0.75 mmol) in tetrahydrofuran (0.5 ml) over 10 minutes. The reaction mixture was allowed to warm to 20° C. over 30 minutes, and then concentrated in vacuo. The crude oil was dissolved in dichloromethane (10 ml) and washed successively with water (2×2 ml), and saturated brine (2 ml) then dried over magnesium sulphate. The solution was filtered then concentrated in vacuo to give an amber oil which was purified by flash chromatography over silica gel eluting with ethyl acetate to yield methyl 2-(4-fluorobenzyloxyimino)-1-pyrid-3-ylcyclohexanecarbodithioate (102 mg).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe crude oil was dissolved in dichloromethane (10 ml)
  3. washwashed successively with water (2×2 ml), and saturated brine (2 ml)
  4. dry with materialthen dried over magnesium sulphate
  5. filtrationThe solution was filtered
  6. concentrationthen concentrated in vacuo
  7. customto give an amber oil which
  8. customwas purified by flash chromatography over silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-1b1e14b99132481dbe24743571ef4327
Source dataset
uspto-grants-1992_09
Patent number
US05151436

Reaction notes

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