Diethyl Ether → HCID 10731993, compound

HRID 568066Notes

Reaction equation

HRID 568066 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][O:15][CH3:16])=[CH:9][CH:8]=1.[Cl:17][Si:18](Cl)([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20].C(OCC)C>C1COCC1>[Cl:17][Si:18]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][O:15][CH3:16])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 2758384DiisopropyldichlorosilaneHCID 104659191-Bromo-4-(methoxymethoxy)benzeneHCID 178418339Butyllithium

Product 1

HCID 10731993HCID 10731993, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of n-butyllithium (1.6M, 72.50 mL, 0.116 mol) was added slowly dropwise to a solution of bromo-4-methoxymethoxybenzene (25.23 g, 0.116 mol) in dry THF (110 mL) at −78° C. After stirring for 50 min at −78° C., dichlorodiisopropylsilane (21.00 mL, 0.116 mol) was charged into the flask. The reaction mixture was slowly allowed to warm to room temperature with stirring. Diethyl ether (100 mL) was added, the mixture was then stirred for 15 min and filtered. The filtrate was concentrated in vacuo to an oil. The oil was purified by short path distillation (116-128° C./0.18 mm Hg) to afford the compound (23.7 g, 71%) as a slightly cloudy pale yellow oil.

Workup

  1. temperatureto warm to room temperature
  2. stirringwith stirring
  3. stirringthe mixture was then stirred for 15 min
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo to an oil
  6. distillationThe oil was purified by short path distillation (116-128° C./0.18 mm Hg)

Sources & evidence

ORD record
ord-e5cb78e6634d4fec98a73bd3ea9c3b16
Source dataset
uspto-grants-2001_01
Patent number
US06180718B2

Reaction notes

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