Benzyl 5-Bromoamyl Ether → 3-(5-Benzyloxypentyl)(1-hexenyl)benzene

HRID 36151Notes

Reaction equation

HRID 36151 reaction equation
C([Li])(C)(C)C.Br[C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:10]=[CH:11][CH:12]=1.Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CCCCCC.O1CCCC1>[CH2:26]([O:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:10]=[CH:11][CH:12]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 14221121Benzyl 5-Bromoamyl EtherHCID 539400723-Bromo-(1-hexenyl)benzeneHCID 178418306HCID 178418306, compound

Product 1

HCID 539255003-(5-Benzyloxypentyl)(1-hexenyl)benzene

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

At -78° C., 27.8 ml of t-butyl lithium (1.7M) in hexane are added to 5.30 gm of 3-bromo-(1-hexenyl)benzene in 75 mls of tetrahydrofuran. The reaction is stirred for 10 minutes, and then 1.1 ml of Li2CuCl3 (0.20M/THF) is added followed dropwise by 5.78 grams of 1-bromo-5-benzyloxy pentane. After allowing the reaction mixture to come to ambient temperature over 5 hours and stirring for an additional 24 hours, silica gel is added; and the mixture is concentrated and then chromatographed (HPLC) to yield pure 3-(5-benzyloxypentyl)-1-(1-hexenyl)benzene.

Workup

  1. waitto come to ambient temperature over 5 hours
  2. stirringstirring for an additional 24 hours
  3. additionsilica gel is added
  4. concentrationand the mixture is concentrated
  5. customchromatographed (HPLC)

Sources & evidence

ORD record
ord-88dd47527ed04c1cb849f65b1525da8b
Source dataset
uspto-grants-1995_05
Patent number
US05412137

Reaction notes

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