2-(6-(Phenyldimethylsilyl)-hexyl)-1,1,2-tribromocyclopropane → 1-(6-(Phenyldimethylsilyl)-hexyl)-cyclopropene

HRID 1265975Notes

Reaction equation

HRID 1265975 reaction equation
[C:1]1([Si:7]([CH3:21])([CH3:20])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]2(Br)[CH2:16][C:15]2(Br)Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Li]>CCOCC>[C:1]1([Si:7]([CH3:21])([CH3:20])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]2[CH2:16][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 185481952-(6-(Phenyldimethylsilyl)-hexyl)-1,1,2-tribromocyclopropaneHCID 178418348HCID 178418348, compound

Product 1

HCID 185481991-(6-(Phenyldimethylsilyl)-hexyl)-cyclopropeneYield 40.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 0.95 g (1.9 mmol) of 2-(6-(phenyldimethylsilyl)-hexyl)-1,1,2-tribromocyclopropane in ether was cooled to −78° C. Excess methyllithium (1.4M, 4.1 ml, 5.7 mmol) was added, and the reaction mixture was placed in an ice bath for 30 min, then quenched with water. The phases were separated. The ether phase was washed with water, washed with brine, dried over magnesium sulfate and stripped to give 200 mg of 1-(6-(phenyldimethylsilyl)-hexyl)-cyclopropene as a colorless liquid.

Workup

  1. customquenched with water
  2. customThe phases were separated
  3. washThe ether phase was washed with water
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-186b8056a43c4562b04966855e1373a6
Source dataset
uspto-grants-2003_04
Patent number
US06548448B2

Reaction notes

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