Sodium Methoxide → HCID 54035311, compound

HRID 479890Notes

Reaction equation

HRID 479890 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6]P(=O)(OCC)OCC)=[CH:4][C:3]=1[O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Cl:24][C:25]1[CH:38]=[CH:37][C:28]([C:29]([CH:34]2[CH2:36][CH2:35]2)=[C:30]([F:33])[CH:31]=O)=[CH:27][CH:26]=1.C[O-].[Na+]>O1CCCC1>[Cl:24][C:25]1[CH:26]=[CH:27][C:28]([C:29]([CH:34]2[CH2:36][CH2:35]2)=[C:30]([F:33])[CH:31]=[CH:6][C:5]2[CH:15]=[CH:16][C:2]([F:1])=[C:3]([O:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:4]=2)=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 11279166Phosphonic acid, [(4-fluoro-3-phenoxyphenyl)methyl]-, diethyl esterHCID 540115002-Fluoro-3-cyclopropyl-3-(p-chlorophenyl)acrylaldehyde

Product 1

HCID 54035311HCID 54035311, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of diethyl (4-fluoro-3-phenoxybenzyl)phosphonate (2.64 g, 7.8 mmol) and p-chloro-β-cyclopropyl-α-fluorocinnamaldehyde (1.35 g, 6 mmol) in tetrahydrofuran (20 ml) is treated with sodium methoxide (562 mg, 9.36 mmol) at 0° C., stirred at room temperature overnight, quenched with 2 N aqueous hydrochloric acid, and extracted with ethyl acetate. The organic extract is washed sequentially with water, 2 N aqueous hydrochloric acid and water, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain a residue. Flash chromatography of the residue on silica gel eluting with 1:9 ethyl acetate/hexanes gives the title product as a syrup (2.15 g, 87.7% yield) which is identified by 1H and 19F NMR spectral analyses.

Workup

  1. customquenched with 2 N aqueous hydrochloric acid
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washis washed sequentially with water, 2 N aqueous hydrochloric acid and water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain a residue

Sources & evidence

ORD record
ord-26f1550f99d347b795f05f2e86f5b3a5
Source dataset
uspto-grants-2003_11
Patent number
US06646166B1

Reaction notes

Loading…