Sodium hydride → HCID 59157923, compound

HRID 1422574Notes

Reaction equation

HRID 1422574 reaction equation
[Br:1][C:2]1[C:11]([I:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:13]P(=O)(OCC)OCC)=[CH:7]2.[H-].[Na+].[CH:24]([C:26]1[CH:27]=[C:28]([CH:33]=[CH:34][CH:35]=1)[C:29]([O:31][CH3:32])=[O:30])=O>C1COCC1>[Br:1][C:2]1[C:11]([I:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](/[CH:13]=[CH:24]/[C:26]1[CH:27]=[C:28]([CH:33]=[CH:34][CH:35]=1)[C:29]([O:31][CH3:32])=[O:30])=[CH:7]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 639145Methyl 3-formylbenzoateHCID 59157922HCID 59157922, compound

Product 1

HCID 59157923HCID 59157923, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of diethyl (5-bromo-6-iodo-2-naphthyl)methylphosphonate (250 mg) from step 5 in THF (5 mL) at 0° C. was added NaH (60% in mineral oil, 17 mg). The reaction mixture was stirred for 1 hour upon which methyl 3-formylbenzoate (85 mg) was added and stirring continued for 1 h at rt. The mixture was quenched with a saturated solution of NH4Cl, extracted with EtOAc, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography eluting with 5% EtOAc/hexanes to afford the titled product.

Workup

  1. additionwas added
  2. customThe mixture was quenched with a saturated solution of NH4Cl
  3. extractionextracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was purified by flash chromatography
  7. washeluting with 5% EtOAc/hexanes

Sources & evidence

ORD record
ord-20dc1d8e71e94067a84490700eeadab2
Source dataset
uspto-grants-2015_01
Patent number
US08927526B2

Reaction notes

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