Sodium hydride → HCID 59157957, compound

HRID 523124Notes

Reaction equation

HRID 523124 reaction equation
[CH2:1]([O:3][P:4]([O-:8])[O:5][CH2:6][CH3:7])[CH3:2].[H-].[Na+].[Br:11][C:12]1[C:13]([C:24]([P:27](=[O:34])([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30])([F:26])[F:25])=[CH:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[C:17]([CH2:22]Br)[CH:16]=2>C1(C)C=CC=CC=1>[CH2:1]([O:3][P:4]([CH2:22][C:17]1[CH:18]=[CH:19][C:20]2[C:15](=[CH:14][C:13]([C:24]([P:27]([O:31][CH2:32][CH3:33])([O:28][CH2:29][CH3:30])=[O:34])([F:26])[F:25])=[C:12]([Br:11])[CH:21]=2)[CH:16]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3780918DiethylphosphiteHCID 59157924HCID 59157924, compound

Product 1

HCID 59157957HCID 59157957, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of diethylphosphite (0.22 mL) in toluene (5 mL) at 0° C. was added NaH (60% in mineral oil, 20 mg). The reaction mixture was stirred for 1 hour and then a solution of diethyl [3-bromo-7-(bromomethyl)-2-naphthyl](difluoro)methylphosphonate (220 mg) in toluene (2 mL) was added dropwise. The reaction was stirred for 1 h at 0° C., quenched with a solution of saturated NH4Cl, extracted with EtOAc and dried over Na2SO4. The organic extracts were evaporated to dryness and the residue was purified by flash chromatography eluting with 50% EtOAc/hexanes to afford the titled compound.

Workup

  1. stirringThe reaction was stirred for 1 h at 0° C.
  2. customquenched with a solution of saturated NH4Cl
  3. extractionextracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. customThe organic extracts were evaporated to dryness
  6. customthe residue was purified by flash chromatography
  7. washeluting with 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-ccc15177bfa94c08ba7e6723fd5bb22a
Source dataset
uspto-grants-2016_05
Patent number
US09334295B2

Reaction notes

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