Diethyl Ether → HCID 178473683, compound

HRID 22206

Reaction equation

HRID 22206 reaction equation
[H-].[Na+].Cl[CH2:4]/[CH:5]=[C:6](/[CH3:13])\[CH2:7][CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11].[CH2:14]([O:16][CH2:17][PH:18]([CH2:20][P:21](=[O:28])([O:25][CH2:26][CH3:27])[O:22][CH2:23][CH3:24])=[O:19])[CH3:15].[I-].[CH3:30][CH2:31]OCC>CN(C=O)C>[CH2:14]([O:16][CH2:17][PH:18]([CH:20]([P:21](=[O:28])([O:22][CH2:23][CH3:24])[O:25][CH2:26][CH3:27])[CH2:30][CH2:31][CH2:4]/[CH:5]=[C:6](/[CH3:13])\[CH2:7][CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])=[O:19])[CH3:15]

Participants

7

Reactant 5

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 30165Iodide IonHCID 5874259Neryl chlorideHCID 178473686HCID 178473686, compound

Product 1

HCID 178473683HCID 178473683, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a stirred mixture of 123 mg (5.13 mmol) of sodium hydride in 10 mL of DMF at 0° C. under argon was added 1.32 g (5.13 mmol) of Example 1, Part A [(ethoxymethylphosphinyl)methyl]phosphonic acid, diethyl ester in 5 mL of DMF dropwise over 20 minutes. The mixture was stirred for 0.5 hours and was treated with 1.00 g (3.42 mmol) of Part A iodide in 3 mL of DMF. The reaction was stirred at 0° C. for 1 hour then at room temperature for 48 hours, at which time the reaction was diluted with ether and quenched with saturated NH4Cl. The organic layer was washed with water, brine, dried (MgSO4) and evaporated to provide 1.10 g of a pale yellow oil. Flash chromatography was performed on 100 g of silica gel eluted with 49.5:49.5:1 acetone/ethyl acetate/methanol (1 liter) followed by 45:45:10 acetone/ethyl acetate/methanol. Pure product fractions were combined and evaporated to provide 600 mg (43%) of title ester as a pale yellow oil, a mixture of diastereomers.

Workup

  1. stirringThe reaction was stirred at 0° C. for 1 hour
  2. waitat room temperature for 48 hours
  3. customquenched with saturated NH4Cl
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-6a90e7ab0f284dfc9b059e1e2c7eb2d0
Source dataset
uspto-grants-1995_06
Patent number
US05428028

Linked notes

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