Ammonium Chloride → HCID 22066299, compound

HRID 269433Notes

Reaction equation

HRID 269433 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 EtherSolvent

Procedure

[7-(3,5-Dimethoxyphenyl)-7-oxo-1-heptynyl]trimethylsilane (1 equiv.) was dissolved in anhydrous ether (0.5 M), the solution was cooled in an ice-bath under argon and methylmagnesium bromide (2 equiv., 3M solution in diethyl ether) was added dropwise. The light gray 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 diethyl ether. The combined organic extracts were dried and ether removed to afford pure [7-(3,5-dimethoxyphenyl)-7-hydroxy-1-octynyl]trimethylsilane as a viscous oil after passing through a short silica gel column, in 95% yield.

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 diethyl ether
  4. customThe combined organic extracts were dried
  5. customether removed

Sources & evidence

ORD record
ord-dc289886a5ae49fca0e72023739d884e
Source dataset
uspto-grants-2008_11
Patent number
US07446229B2

Reaction notes

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