Ethyl Acetate → [1-Cyano-2-(tetrahydro-pyran-4-yl)-ethyl]-phosphonic acid diethyl ester

HRID 658060Notes

Reaction equation

HRID 658060 reaction equation
[CH2:1]([O:3][P:4]([C:9]([C:17]#[N:18])=[CH:10][CH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[BH4-].[Na+].[OH-].[Na+].C(OCC)(=O)C>CO>[CH2:1]([O:3][P:4]([CH:9]([C:17]#[N:18])[CH2:10][CH:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 72481733[1-Cyano-2-(tetrahydro-pyran-4-yl)-vinyl]-phosphonic acid diethyl ester

Product 1

HCID 86634265[1-Cyano-2-(tetrahydro-pyran-4-yl)-ethyl]-phosphonic acid diethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of [1-cyano-2-(tetrahydro-pyran-4-yl)-vinyl]-phosphonic acid diethyl ester (7.45 g, 27.1 mmol) in methanol (200 mL) was added sodium borohydride (5 g, 135 mmol, 5 pellets), portion wise over 1.5 hours. The resulting mixture was stirred an additional 2 hours. The solvent was evaporated in vacuo to yield an oil, to which was added 0.1N NaOH and ethyl acetate. The layers were separated, and the organic layer was dried with MgSO4 and filtered. The solvent was removed to yield an oil which was purified via silica column chromatography (50% EtOAc/heptane) to yield an oil.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customto yield an oil
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried with MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed
  7. customto yield an oil which
  8. customwas purified via silica column chromatography (50% EtOAc/heptane)
  9. customto yield an oil

Sources & evidence

ORD record
ord-4b6db4dfbb044098bc14da3628564532
Source dataset
uspto-grants-2011_12
Patent number
US08076358B2

Reaction notes

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