Diethyl Ether → HCID 57826337, compound

HRID 1665849Notes

Reaction equation

HRID 1665849 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([O:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:18]#N)=[CH:13][CH:12]=1.C([O:27]CC)C>>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([O:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:18]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:27])=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 3283Diethyl Ether2×HCID 10776145HCID 10776145, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 57826337HCID 57826337, compoundYield 85%

Procedure

To a diluted solution of 3.0 M phenylmagnesium bromide (Aldrich, 39 mL, 0.12 mol) in anhydrous diethyl ether (500 mL) was slowly added a solution of (4-methoxyphenyl)-trimethylsilanyloxy-acetonitrile (36.13 g, 0.11 mol), which obtained in Step 1, in anhydrous diethyl ether (50 mL) at 4° C. After addition was complete, the reaction solution was elevated to room temperature and stirred for 2 hours. The reaction was quenched by slow addition of 3N HCl solution (200 ml). After separation of an organic layer and aqueous layer, the thus-obtained organic layer was washed twice with 100 mL of a saturated sodium bicarbonate solution and then successively washed twice with 100 mL of a brine solution. The organic layer obtained was dried over magnesium sulfate, filtered and concentrated under reduced pressure, to give 30.54 g (yield: 85%) of 2-(4-methoxyphenyl)-1-phenyl-2-trimethylsilanyloxy-ethanone as a desired product.

Workup

  1. additionAfter addition
  2. customwas elevated to room temperature
  3. customThe reaction was quenched by slow addition of 3N HCl solution (200 ml)
  4. customAfter separation of an organic layer and aqueous layer
  5. washthe thus-obtained organic layer was washed twice with 100 mL of a saturated sodium bicarbonate solution
  6. washsuccessively washed twice with 100 mL of a brine solution
  7. customThe organic layer obtained
  8. dry with materialwas dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-94453750e0d942b88275710670da1da1
Source dataset
uspto-grants-2011_10
Patent number
US08039634B2

Reaction notes

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