Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → 3-(2-Propylamino-4-trifluoromethyl-phenyl)-acrylic acid methyl ester

HRID 1042447Notes

Reaction equation

HRID 1042447 reaction equation
[CH2:1]([NH:4][C:5]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:6]=1[CH:7]=O)[CH2:2][CH3:3].[CH3:17][O:18][C:19]([CH:21]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:20]>C1(C)C=CC=CC=1>[CH3:17][O:18][C:19](=[O:20])[CH:21]=[CH:7][C:6]1[CH:9]=[CH:10][C:11]([C:13]([F:16])([F:15])[F:14])=[CH:12][C:5]=1[NH:4][CH2:1][CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 866499552-Propylamino-4-trifluoromethyl-benzaldehyde

Product 1

HCID 668555113-(2-Propylamino-4-trifluoromethyl-phenyl)-acrylic acid methyl esterYield 69%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-Methoxy-N-methyl-2-propylamino-4-trifluoromethyl-benzamide (98.3 mg, 0.339 mmol) was reacted with 1M lithium aluminum hydride (0.6 ml) in THF (20 ml) at −40° C. for 1 hr. The reaction mixture was quenched by adding saturated potassium hydrogen sulfate solution. The mixture was stirred for 30 min. The reactions solvent was removed in vacuo. Water (30 ml) was added to the resulting residue, which was extracted with CH2Cl2 (30 ml×3). The combined organic layer was dried over MgSO4 and concentrated in vacuo to yield 2-propylamino-4-trifluoromethyl-benzaldehyde (78 mg). 2-Propylamino-4-trifluoromethyl-benzaldehyde in toluene was reacted with methyl (triphenylphosphoranylidene) acetate (137 mg) at 100° C. overnight. The reaction solvent was removed in vacuo. Water (30 ml) was added to the resulting residue, which was extracted with ethyl acetate (30 ml×3). The combined organic layer was dried over MgSO4 and filtered. The filterate was concentrated in vacuo and purified with column chromatography to yield title compound (67 mg, 69%).

Workup

  1. customThe reaction solvent was removed in vacuo
  2. additionWater (30 ml) was added to the resulting residue, which
  3. extractionwas extracted with ethyl acetate (30 ml×3)
  4. dry with materialThe combined organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationThe filterate was concentrated in vacuo
  7. custompurified with column chromatography

Sources & evidence

ORD record
ord-1c192df185334e51889354a6eb57f9fa
Source dataset
uspto-grants-2013_10
Patent number
US08557872B2

Reaction notes

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