Pyridine → 863506-85-8

HRID 2354982Notes

Reaction equation

HRID 2354982 reaction equation
[CH2:1]([C:8]1([CH2:11]O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.C(Br)(Br)(Br)[Br:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:20][CH2:11][C:8]1([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:10][CH2:9]1

Participants

7

Reactant 5

HCID 1049PyridineHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 561876(1-benzylcyclopropyl)methanol

Product 1

HCID 59382362863506-85-8

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the title C compound, (1-benzyl-cyclopropyl)-methanol (0.8 g, 4.93 mmol), pyridine (994 uL, 12.3 mmol) and CBr4 (1.8 g, 5.42 mmol) in methylene chloride (25 mL) is added triphenylphosphine (1.8 g, 6.9 mmol), with stirring at 0° C. After completion of the reaction, the mixture is poured into a saturated aqueous solution of NaHCO3. The aqueous layer is extracted twice with methylene chloride and the combined organic extracts are dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue is taken up into ether and the triphenylphosphine oxide precipitate is filtered off. The filtrate is concentrated under reduced pressure and purified by flash column chromatography on silica gel (hexane/EtOAc 9/1) to afford the title compound: TLC, Rf (hexane/AcOEt 99/1)=0.54. Rt (HPLC, Nucleosil C18, 10:90-100:0 CH3CN/H2O+0.1% TFA within 5 min, then 100% CH3CN+0.1% TFA): 6.41 min.

Workup

  1. customAfter completion of the reaction
  2. extractionThe aqueous layer is extracted twice with methylene chloride
  3. dry with materialthe combined organic extracts are dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. filtrationthe triphenylphosphine oxide precipitate is filtered off
  6. concentrationThe filtrate is concentrated under reduced pressure
  7. custompurified by flash column chromatography on silica gel (hexane/EtOAc 9/1)

Sources & evidence

ORD record
ord-c30fe285160248c389c078e0260b32e1
Source dataset
uspto-grants-2010_07
Patent number
US07754727B2

Reaction notes

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