Tributylvinyltin → HCID 22935206, compound

HRID 919308Notes

Reaction equation

HRID 919308 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1.[CH:12]([Sn](CCCC)(CCCC)CCCC)=[CH2:13]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([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>[CH:12]([C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1)=[CH2:13]

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 131692632-Chloro-5,6,7,8-tetrahydroquinoline

Product 1

HCID 22935206HCID 22935206, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of 2-chloro-5,6,7,8-tetrahydroquinoline (3.69 g, 22 mmol) and vinyl tributyl tin (7.7 mL, 33 mmol) in toluene (60 mL) was treated with Pd(PPh3)4 (2.5 g, 2.2 mmol) and heated to reflux overnight. The reaction mixture was concentrated and the resulting material was purified directly by gradient elution on silica gel (0 to 20% EtOAc in hexanes) to afford the title compound as a colorless oil. LRMS m/z (M+H) 160.2 found, 160.1 required.

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. concentrationThe reaction mixture was concentrated
  4. customthe resulting material was purified directly by gradient elution on silica gel (0 to 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f04b5d81594a413e92f9357bcf13a903
Source dataset
uspto-grants-2016_03
Patent number
US09273033B2

Reaction notes

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