Trimethylsilyl (diethoxyphosphinoyl)acetate → HCID 53796111, compound

HRID 1281053Notes

Reaction equation

HRID 1281053 reaction equation
C(OP([CH2:9][C:10]([O:12][Si](C)(C)C)=[O:11])(OCC)=O)C.C([Li])CCC.[N+:22]([C:25]1[CH:54]=[C:53]([N+:55]([O-:57])=[O:56])[CH:52]=[CH:51][C:26]=1[O:27][CH2:28][C:29]([F:50])([F:49])[C:30]([F:48])([F:47])[C:31]([F:46])([F:45])[C:32]([F:44])([F:43])[CH2:33][O:34][C:35]1[CH:42]=[CH:41][C:38]([CH:39]=O)=[CH:37][CH:36]=1)([O-:24])=[O:23]>O1CCCC1.CCCCCC.O>[N+:22]([C:25]1[CH:54]=[C:53]([N+:55]([O-:57])=[O:56])[CH:52]=[CH:51][C:26]=1[O:27][CH2:28][C:29]([F:49])([F:50])[C:30]([F:47])([F:48])[C:31]([F:45])([F:46])[C:32]([F:43])([F:44])[CH2:33][O:34][C:35]1[CH:36]=[CH:37][C:38]([CH:39]=[CH:9][C:10]([OH:12])=[O:11])=[CH:41][CH:42]=1)([O-:24])=[O:23]

Participants

7

Reactant 3

HCID 171755Trimethylsilyl (diethoxyphosphinoyl)acetateHCID 18546637HCID 18546637, compoundHCID 178418339Butyllithium

Product 1

HCID 53796111HCID 53796111, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a mixture of trimethylsilyl diethylphosphonoacetate (2.97 g) in anhydrous tetrahydrofuran (100 mL) at 0° C. is added 1.6 M solution of butyllithium in hexane (6.9 mL). The reaction is stirred for 2 hrs. at room temperature and then treated with 4-[6-(2,4-dinitrophenoxy)-2,2,3,3,4,4,5,5-octaflurohexyloxy]benzaldehyde (5.32 g) in anhydrous tetrahydrofuran (30 mL). The mixture is stirred for a further 2 hrs., diluted with water and extracted with ethyl ether. The extracts are washed with water and brine, dried (MgSO4), concentrated, and purified by crystallization to give 4-[6-(2,4-dinitrophenoxy)-2,2,3,3,4,4,5,5-octaflurohexyloxy]cinnamic acid. The acid is converted to the methyl ester by treatment with diazomethane in ether solution.

Workup

  1. stirringThe mixture is stirred for a further 2 hrs
  2. extractionextracted with ethyl ether
  3. washThe extracts are washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. custompurified by crystallization

Sources & evidence

ORD record
ord-8b6c4ad6a7424040896bf0ee47a7d5c1
Source dataset
uspto-grants-2002_09
Patent number
US06451960B1

Reaction notes

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