Ammonium Chloride → HCID 22066299, compound

HRID 496308Notes

Reaction equation

HRID 496308 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=[O:22])[CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[C:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[CH3:23][Mg]Br.[Cl-].[NH4+]>CCOCC>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([C:11]([OH:22])([CH3:23])[CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[C:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 22066286HCID 22066286, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 22066299HCID 22066299, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

[7-(3,5-Dimetho-xyphenyl)-7-oxo-1-heptynyl]trimethysilane (1.50 g, 4.75 mmol) was dissolved in 10 mL of anhydrous ether, the solution was cooled in an ice-bath under argon and a 3.16 mL of a 3 M solution of methylmagnesium bromide (9.48 mmol) in ether was added dropwise. The light grey solution was allowed to warm to room temperature and stirred for an additional hour. The reaction mixture was poured into saturated ammonium chloride solution, the organic phase was separated and the aqueous phase was extracted with fresh diethyl ether. The combined ether extracts were dried and ether removed to afford 1.50 g (95%) of pure [7-(3,5-dimethoxyphenyl)-7-hydroxy-1-octynyl]trimethysilane as a viscous oil after passing through a short silica gel column.

Workup

  1. temperaturethe solution was cooled in an ice-bath under argon
  2. customthe organic phase was separated
  3. extractionthe aqueous phase was extracted with fresh diethyl ether
  4. dry with materialThe combined ether extracts were dried
  5. customether removed

Sources & evidence

ORD record
ord-8005363645844c28b85fcb5975d781af
Source dataset
uspto-grants-2005_09
Patent number
US06943266B1

Reaction notes

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