Ammonium Chloride → HCID 66906874, compound

HRID 1690620Notes

Reaction equation

HRID 1690620 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1[O:15][Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])[CH:10]=[O:11].[CH3:26][Mg]Cl.[Cl-].[NH4+]>O1CCCC1>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:10]([OH:11])[CH3:26])[CH:12]=[CH:13][C:14]=1[O:15][Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 866333003-(3-Methoxypropoxy)4-[(triisopropylsilyl)oxy]benzaldehydeHCID 178418332HCID 178418332, compound

Product 1

HCID 66906874HCID 66906874, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

3-(3-methoxypropoxy)-4-[(triisopropylsilyl)oxy]benzaldehyde (12 g, 32.7 mmol) was dissolved in tetrahydrofuran (300 mL) and the solution was cooled to 0° C. Methyl magnesium chloride (109 mL, 327 mmol) was added dropwise. The temperature was then allowed to rise to room temperature and the mixture was stirred an hour. At 0° C., saturated aqueous ammonium chloride was added to hydrolyze the reaction mixture. The aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to yield 12.5 g (quantitative yield) of the desired product as a yellow oil.

Workup

  1. customto rise to room temperature
  2. extractionThe aqueous layer was extracted twice with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-94985d641689469684fb226d91bbfb11
Source dataset
uspto-grants-2012_04
Patent number
US08153647B2

Reaction notes

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