Water → HCID 58292877, compound

HRID 511212Notes

Reaction equation

HRID 511212 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])[CH3:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].I[CH3:23].O>C1COCC1.CCOC(C)=O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([P:12](=[O:19])([O:13][CH2:14][CH3:15])[O:16][CH2:17][CH3:18])([CH3:23])[CH3:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58292996HCID 58292996, compound

Product 1

HCID 58292877HCID 58292877, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of diethyl [1-(4-nitrophenyl)ethyl]phosphonate (206 mg, 0.717 mmol) in THF (5 mL) at room temperature under N2, was treated portionwise with NaH (60% in mineral oil, 143 mg, 3.58 mmol). The resulting mixture was stirred for 5 min then iodomethane (0.268 mL, 4.30 mmol) was added dropwise and the mixture stirred for a further 5 h. Water (10 mL) was added slowly followed by EtOAc (20 mL). The layers were separated and the aqueous phase extracted with EtOAc (3×20 mL). The organic phases were combined, dried (MgSO4), concentrated in vacuo, and the residue purified by chromatography over silica gel eluting with 5% MeOH in dichloromethane to afford 103 mg of desired diethyl [2-(4-nitrophenyl)propan-2-yl]phosphonate (yield: 48%). 1H-NMR (CD3OD, 400 MHz): δ=1.22 (t, J=7.2 Hz, 6 H), 1.64 (s, 3 H), 1.69 (s, 3 H), 3.94-4.01 (m, 4 H), 7.78 (dd, J=2.4, 9.2 Hz, 2 H), 8.21 (dd, J=0.8, 8.8 Hz, 2 H). MS (ES+): m/z 302.11 (MH+). HPLC: tR=1.44 min (UPLC TOF, polar).

Workup

  1. stirringthe mixture stirred for a further 5 h
  2. customThe layers were separated
  3. extractionthe aqueous phase extracted with EtOAc (3×20 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customthe residue purified by chromatography over silica gel eluting with 5% MeOH in dichloromethane

Sources & evidence

ORD record
ord-cdcc555f668d4935bc9c5d329489abaa
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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