Iodine → [1-Cyano-2-(tetrahydro-pyran-4-yl)-hex-5-enyl]-phosphonic acid diethyl ester

HRID 252440Notes

Reaction equation

HRID 252440 reaction equation
II.Br[CH2:4][CH2:5][CH:6]=[CH2:7].[CH2:8]([O:10][P:11]([C:16]([C:24]#[N:25])=[CH:17][CH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)(=[O:15])[O:12][CH2:13][CH3:14])[CH3:9].[NH4+].[Cl-]>C1COCC1.[Cu]I.C(OCC)(=O)C>[CH2:8]([O:10][P:11]([CH:16]([C:24]#[N:25])[CH:17]([CH:18]1[CH2:19][CH2:20][O:21][CH2:22][CH2:23]1)[CH2:7][CH2:6][CH:5]=[CH2:4])(=[O:15])[O:12][CH2:13][CH3:14])[CH3:9]

Participants

8

Reactant 4

HCID 807IodineHCID 21241Homoallyl bromideHCID 25517Ammonium ChlorideHCID 72481733[1-Cyano-2-(tetrahydro-pyran-4-yl)-vinyl]-phosphonic acid diethyl ester

Product 1

HCID 59428163[1-Cyano-2-(tetrahydro-pyran-4-yl)-hex-5-enyl]-phosphonic acid diethyl ester

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

In a reaction flask, Mg (5.7 g) was placed in THF (50 mL) with an iodine chip. The reaction mixture was stirred vigorously, as 4-bromobutene (25 mL) was added. The reaction mixture was then heated slightly. After consumption of the Mg metal, the reaction mixture was cannulated into a flask containing a mixture of [1-cyano-2-(tetrahydro-pyran-4-yl)-vinyl]-phosphonic acid diethyl ester (21.78 g, 79.7 mmol) and CuI (0.3 g) in THF (30 mL). The reaction mixture was stirred for three hours and then worked up with saturated aqueous NH4Cl and ethyl acetate. The layers were separated, and the organic layer was dried with MgSO4, filtered, and evaporated in vacuo to yield the title compound as an oil.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was then heated slightly
  3. customAfter consumption of the Mg metal
  4. customthe reaction mixture was cannulated into a flask
  5. additioncontaining
  6. customThe layers were separated
  7. dry with materialthe organic layer was dried with MgSO4
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-8de3c5a9d79b416684503baf3e524f3d
Source dataset
uspto-grants-2011_01
Patent number
US07868022B2

Reaction notes

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