Diethyl Ether → HCID 67085016, compound

HRID 1047457Notes

Reaction equation

HRID 1047457 reaction equation
[C:1]([Si:5]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[O:6][CH:7]1[CH:11]([CH2:12][O:13][C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:10](OS(C(F)(F)F)(=O)=O)=[CH:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[CH3:53][Si:54]([Mg]Cl)([CH3:56])[CH3:55].[CH2:59](OCC)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([Si:5]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[O:6][C:7]1([CH2:53][Si:54]([CH3:56])([CH3:59])[CH3:55])[CH2:8][CH2:9][CH:10]=[C:11]1[CH2:12][O:13][C:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 86669102HCID 86669102, compoundHCID 178504298HCID 178504298, compound

Product 1

HCID 67085016HCID 67085016, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
0 °C

Procedure

The enolate compound of formula (X) obtained in Example 1-1 (33.5 g, 45.1 mmol) was dissolved in diethylether (335 ml). Tetrakis(triphenylphosphine)palladium (2.6 g, 2.25 mmol) was added thereto at room temperature and cooled to 0° C. To the resulting mixture, 1 M trimethylsilyl magnesium chloride (90.2 ml, 90.2 mmol) was added and stirred at room temperature for 1 hr. After completion of the reaction, the resulting mixture was cooled to 0° C. The cooled mixture was quenched with saturated sodium bicarbonate (335 ml) and filtered through Celite. The resulting solid was washed with ethyl acetate, dried over anhydrous sodium sulfate, filtered, and condensed under a reduced pressure. The material thus obtained was purified with column chromatography to obtain the title compound (26.99 g, yield: 87.4%).

Workup

  1. customAfter completion of the reaction
  2. temperaturethe resulting mixture was cooled to 0° C
  3. customThe cooled mixture was quenched with saturated sodium bicarbonate (335 ml)
  4. filtrationfiltered through Celite
  5. washThe resulting solid was washed with ethyl acetate
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customcondensed under a reduced pressure
  9. customThe material thus obtained
  10. customwas purified with column chromatography

Sources & evidence

ORD record
ord-160a20be88474f29a261fe97dacf170a
Source dataset
uspto-grants-2013_10
Patent number
US08569491B2

Reaction notes

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