Chloromethyl ethyl ether → HCID 19767442, compound

HRID 372952Notes

Reaction equation

HRID 372952 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[NH:4][CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[H-].[Na+].[CH2:14]([O:16][CH2:17]Cl)[CH3:15]>O1CCCC1.C(OCC)(=O)C.CCCCCC>[CH2:14]([O:16][CH2:17][N:4]1[CH:5]=[CH:6][C:7]([C:8]#[N:9])=[C:3]1[C:2]([F:1])([F:10])[F:11])[CH3:15]

Participants

7

Reactant 3

HCID 18523Chloromethyl ethyl etherHCID 24758Sodium hydrideHCID 15150705HCID 15150705, compound

Product 1

HCID 19767442HCID 19767442, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A stirred solution of 2-trifluoromethyl-3-cyanopyrrole (1.0 g, 6.2 mmol) in dry tetrahydrofuran is treated with NaH (0.30 g, 7.5 mmol) as a 60% dispersion in mineral oil, under nitrogen, at room temperature. After 20 minutes, the reaction mixture is treated dropwise with a solution of chloromethyl ethyl ether (0.77 g, 8.1 mmol) in dry tetrahydrofuran, stirred vigorously for 3 hours and treated with a mixture of 1N HCI and ethyl acetate. The phases are separated and the organic phase is washed with brine, dried over Mg SO4 and concentrated in vacuo to afford a residue. Flash chromatography of the residue using silica gel and 3.5:1 hexane: ethyl acetate yields the title compound as a pale yellow oil, 0.83 g (61%).

Workup

  1. customThe phases are separated
  2. washthe organic phase is washed with brine
  3. dry with materialdried over Mg SO4
  4. concentrationconcentrated in vacuo
  5. customto afford a residue

Sources & evidence

ORD record
ord-1d5bf93f46184343864e7abd5a423c8f
Source dataset
uspto-grants-1992_11
Patent number
US05162308

Reaction notes

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