Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 66856006, compound

HRID 1042452Notes

Reaction equation

HRID 1042452 reaction equation
[CH2:1]([O: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].C1(P(=[CH:36][C:37]([O:39][CH3:40])=[O:38])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:40][O:39][C:37](=[O:38])[CH:36]=[CH:7][C:6]1[CH:9]=[CH:10][C:11]([C:13]([F:16])([F:15])[F:14])=[CH:12][C:5]=1[O:4][CH2:1][CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 22494266HCID 22494266, compound

Product 1

HCID 66856006HCID 66856006, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Propoxy-4-trifluoromethyl-benzaldehyde (232 mg, 1 mmol) in toluene was reacted with methyl (triphenylphosphoranylidene)acetate (382 mg, 1.14 mmol) at 110° C. overnight. The reaction solvent was removed under reduced pressure. Water (30 ml) was added to the resulting residue, which was extracted with ethyl acetate (30 ml×3). The combined organic layer was washed with brine (30 ml) and dried over MgSO4. The filterate was purified with column chromatography to yield title compound (198 mg, 69%).

Workup

  1. customThe reaction solvent was removed under reduced pressure
  2. additionWater (30 ml) was added to the resulting residue, which
  3. extractionwas extracted with ethyl acetate (30 ml×3)
  4. washThe combined organic layer was washed with brine (30 ml)
  5. dry with materialdried over MgSO4
  6. customThe filterate was purified with column chromatography

Sources & evidence

ORD record
ord-86ee30bd098048c888a821183d88161a
Source dataset
uspto-grants-2013_10
Patent number
US08557872B2

Reaction notes

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