1-Chloro-3-methyl-2-butene → HCID 86657323, compound

HRID 1621058Notes

Reaction equation

HRID 1621058 reaction equation
[CH2:1]([P:3]([O-:9])[O:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH3:2].N12CCCN=C1CCCCC2.Cl[CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25]>C1C=CC([P]([Ni]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH2:1]([P:3]([CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])(=[O:9])[O:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH3:2]

Participants

6

Reactant 3

HCID 104291-Chloro-3-methyl-2-buteneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86614949Butyl ethyiphosphonite

Product 1

HCID 86657323HCID 86657323, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 178420538HCID 178420538, compoundCatalystHCID 1140TolueneSolvent

Procedure

At room temperature, a three-neck flask equipped with stirrer and high-performance condenser is initially charged with 400 g of toluene and this initial charge is devolatilized by stirring and passing nitrogen through it. Then, under nitrogen, 6.65 g (6 mmol) of tetrakis(triphenylphosphine)nickel and 30 g (0.2 mol) of butyl ethylphosphonite (produced as in Example 2) and 30.4 g (0.2 mol) of 1,8-diazabicyclo[5.4.0]undec-7-ene are added followed by the dropwise addition of 20.9 g (0.2 mol) of 1-chloro-3-methyl-2-butene. Following a reaction time of 5 hours, the reaction solution is passed for purification through a column charged with Deloxan® THP Hand the solvent is removed in vacuo. The product is purified by column chromatography to obtain 33.1 g (76% of theory) of butyl ethyl(3-methyl-2-butenyl)phosphinate as colorless oil.

Workup

  1. customAt room temperature, a three-neck flask equipped with stirrer and high-performance condenser
  2. additionthis initial charge
  3. customa reaction time of 5 hours
  4. customthe reaction solution is passed for purification through a column
  5. additioncharged with Deloxan® THP Hand the solvent
  6. customis removed in vacuo
  7. customThe product is purified by column chromatography

Sources & evidence

ORD record
ord-368c7e2cea5f406ea471dbc6d118819f
Source dataset
uspto-grants-2014_07
Patent number
US08772519B2

Reaction notes

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