((5-Bromopentyl)oxy)(tert-butyl)dimethylsilane → HCID 178455214, compound

HRID 258182Notes

Reaction equation

HRID 258182 reaction equation
BrC[CH2:3][CH2:4][CH2:5][CH2:6][O:7][Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9].[CH3:15][Mg+:16].[Br-:17]>O(CC)CC>[CH3:13][C:11]([Si:8]([CH3:9])([CH3:10])[O:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:15][Mg:16][Br:17])([CH3:12])[CH3:14]

Participants

4

Reactant 2

HCID 14381200((5-Bromopentyl)oxy)(tert-butyl)dimethylsilaneHCID 178418689HCID 178418689, compound2×

Product 1

HCID 178455214HCID 178455214, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of Mg turnings (0.6 g, 24 mmole), [(5-bromo-1-pentyl)oxy]-(1,1-dimethylethyl)dimethylsilane (0.5 mL), and MeMgBr (0.2 mL, 3 M) in dry OEt2 (5 mL) was stirred and heated to reflux for 5 minutes under an inert atmosphere. A solution of [(5-bromo-10-pentyl)oxy](1,1-dimethyl-ethyl)dimethylsilane (5.62 g, 20 mmole) and MeMgBr (0.2 mL, 3 M) in dry OEt2 (20 mL) was added dropwise at a rate to maintain a gentle, unassisted reflux. After addition was complete, the reaction was heated at reflux for 45 minutes. The solution of Grignard reagent was then cooled and used immediately in the next reaction.

Workup

  1. temperatureheated
  2. temperatureto reflux for 5 minutes under an inert atmosphere
  3. temperatureto maintain a gentle, unassisted reflux
  4. additionAfter addition
  5. temperaturethe reaction was heated
  6. temperatureat reflux for 45 minutes
  7. customused immediately in the next reaction

Sources & evidence

ORD record
ord-74a3729d9a7b4c5d99c1e195bd1bc45c
Source dataset
uspto-grants-1993_11
Patent number
US05264619

Reaction notes

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