Methyl 3-formylbenzoate → HCID 86638320, compound

HRID 1422577Notes

Reaction equation

HRID 1422577 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]([P:15]([O:20][CH2:21][CH3:22])([O:17][CH2:18][CH3:19])=[O:16])([F:14])[F:13])[CH:8]=[C:7]([CH2:23]P(=O)(OCC)OCC)[CH:6]=[CH:5]2.[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:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]([P:15]([O:17][CH2:18][CH3:19])([O:20][CH2:21][CH3:22])=[O:16])([F:14])[F:13])[CH:8]=[C:7](/[CH:23]=[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:6]=[CH:5]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-c9a222b13eb74d3b908c5d5bfba89630
Source dataset
uspto-grants-2015_01
Patent number
US08927526B2

Reaction notes

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