Methyl 3-formylbenzoate → HCID 86638320, compound

HRID 1920520Notes

Reaction equation

HRID 1920520 reaction equation
C(OP([CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][C:14]([C:21]([P:24]([O:29][CH2:30][CH3:31])([O:26][CH2:27][CH3:28])=[O:25])([F:23])[F:22])=[C:15]([Br:20])[CH:16]=2)[CH:11]=1)(=O)OCC)C.[CH:32]([C:34]1[CH:35]=[C:36]([CH:41]=[CH:42][CH:43]=1)[C:37]([O:39][CH3:40])=[O:38])=O.CC(C)([O-])C.[K+]>C1COCC1>[Br:20][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][C:14]=1[C:21]([P:24]([O:26][CH2:27][CH3:28])([O:29][CH2:30][CH3:31])=[O:25])([F:23])[F:22])[CH:11]=[C:10](/[CH:9]=[CH:32]/[C:34]1[CH:35]=[C:36]([CH:41]=[CH:42][CH:43]=1)[C:37]([O:39][CH3:40])=[O:38])[CH:19]=[CH:18]2

Participants

5

Reactant 3

HCID 639145Methyl 3-formylbenzoateHCID 23665647Potassium tert-butoxideHCID 59157957HCID 59157957, compound

Product 1

HCID 86638320HCID 86638320, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of diethyl{6-bromo-7-[(diethoxyphosphoryl)(difluoro)methyl]-2-naphthyl}methylphosphonate (190 mg), and methyl 3-formylbenzoate (60 mg) in degassed THF (5 mL) at −78° C. was added potassium tert-butoxide (0.35 mL of a 1M solution in THF) and the reaction mixture was stirred for 1 h at 0° C. The mixture was quenched with a saturated solution of NH4Cl, extracted with EtOAc, dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography eluting with 25% EtOAc/hexanes to afford the titled product.

Workup

  1. customThe mixture was quenched with a saturated solution of NH4Cl
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness
  5. customThe residue was purified by flash chromatography
  6. washeluting with 25% EtOAc/hexanes

Sources & evidence

ORD record
ord-8bb675b489354f9fa930397a5430c160
Source dataset
uspto-grants-2012_05
Patent number
US08168815B2

Reaction notes

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