Dichloromethane → HCID 70149708, compound

HRID 990540Notes

Reaction equation

HRID 990540 reaction equation
[OH-].[Na+].[F:3][C:4]([F:15])([F:14])[O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)C=O.[O:16]=[C:17]([CH3:27])[CH2:18]P(=O)(OCC)OCC.[CH2:28](Cl)Cl>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:15][C:4]([F:3])([F:14])[O:5][C:6]1[CH:13]=[CH:12][CH:11]=[CH:8][C:7]=1[CH:28]=[CH:18][C:17](=[O:16])[CH3:27]

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 140281-Diethoxyphosphorylpropan-2-oneHCID 14798Sodium HydroxideHCID 6051393-(Trifluoromethoxy)benzaldehyde

Product 1

HCID 70149708HCID 70149708, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

Tetrabutylammonium iodide (0.4 g, 0.05 mol) was added to a well-stirred biphasic mixture of 12 mL of 50% NaOH and 20 mL of methylene chloride under a nitrogen atmosphere. A solution of 3-trifluoromethoxybenzaldehyde (4.0 g, 0.021 mol) and diethyl (2-oxopropyl)phosphonate (4.08 g, 0.021 mol) in 4.0 mL of methylene chloride was added dropwise to the stirred solution. The resulting mixture was stirred at room temperature for 15 min, then quenched with water and extracted with hexane. The hexane layer was dried over MgSO4. The crude product was purified by flash column chromatography on silica gel eluting with 1:10 ethyl acetate in hexane to give 2.6 g (54%) of the desired 4[-(trifluoromethoxy)phenyl]-3-buten-2-one product as a yellow oil. 1H NMR (CDCl3) δ7.43 (m, 4H), 7.20 (d, 1H), 6.65 (d, 2H), 2.29 (s, 3H). 19F NMR (CDCl3) δ−62.05 (s, 3F).

Workup

  1. customquenched with water
  2. extractionextracted with hexane
  3. dry with materialThe hexane layer was dried over MgSO4
  4. customThe crude product was purified by flash column chromatography on silica gel eluting with 1:10 ethyl acetate in hexane

Sources & evidence

ORD record
ord-b485108bf0714e50b08b7c8da93aa274
Source dataset
uspto-grants-2002_10
Patent number
US06458852B1

Reaction notes

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