Sodium hydride → HCID 66906859, compound

HRID 1690622Notes

Reaction equation

HRID 1690622 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:22])[CH2:7]P(OCC(F)(F)F)(OCC(F)(F)F)=O)[CH3:4].[CH3:23][O:24][CH2:25][CH2:26][CH2:27][O:28][C:29]1[CH:30]=[C:31]([C:46](=O)[CH3:47])[CH:32]=[CH:33][C:34]=1[O:35][Si:36]([CH:43]([CH3:45])[CH3:44])([CH:40]([CH3:42])[CH3:41])[CH:37]([CH3:39])[CH3:38].[Cl-].[NH4+]>C(COC)OC>[CH3:23][O:24][CH2:25][CH2:26][CH2:27][O:28][C:29]1[CH:30]=[C:31]([C:46]([CH3:47])=[CH:7][C:6]([O:5][CH2:3][CH3:4])=[O:22])[CH:32]=[CH:33][C:34]=1[O:35][Si:36]([CH:43]([CH3:45])[CH3:44])([CH:40]([CH3:42])[CH3:41])[CH:37]([CH3:38])[CH3:39]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 11759356Ethyl [bis(2,2,2-trifluoroethoxy)phosphinyl]acetateHCID 66906571HCID 66906571, compound

Product 1

HCID 66906859HCID 66906859, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

In a three-necked round bottom flask, sodium hydride 60% (1.04 g, 26.0 mmol) was suspended in dimethoxyethane (15 mL) at 0° C. Ethyl[bis(2,2,2-trifluoroethoxy)phosphinyl]acetate (8.63 g, 26.0 mmol) was added and the mixture was stirred at room temperature for 15 minutes. A solution of 1-{3-(3-methoxypropoxy)-4-[(triisopropylsilyl)oxy]phenyl}ethanone (6.60 g, 17.3 mmol) and dimethoxyethane (20 mL) was added and the mixture was brought to reflux and stirred for 1 hr. The reaction mixture was hydrolyzed with saturated aqueous ammonium chloride (80 mL). The aqueous layer was extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 8/2) to yield 7.5 g (81%) of the desired product as a colorless oil of a mixture of E and Z isomers.

Workup

  1. temperatureto reflux
  2. stirringstirred for 1 hr
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×100 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 8/2)
  9. customto yield

Sources & evidence

ORD record
ord-05a67df53643499da82bf584bfbc1635
Source dataset
uspto-grants-2012_04
Patent number
US08153647B2

Reaction notes

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