Allyl Alcohol → HCID 86628371, compound

HRID 553279Notes

Reaction equation

HRID 553279 reaction equation
[C:1]([O:5][C:6](=[O:26])[N:7]([CH2:16][CH2:17][C:18]1[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:25])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](I)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].[CH2:32]([OH:35])[CH:33]=[CH2:34]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:26])[N:7]([CH2:16][CH2:17][C:18]1[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:25])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:34][CH2:33][CH:32]=[O:35])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 7858Allyl AlcoholHCID 516892Sodium BicarbonateHCID 67165818[2-(2,6-Dichloro-phenyl)-ethyl]-(3-iodo-benzyl)-carbamic acid tert-butyl ester

Product 1

HCID 86628371HCID 86628371, compound

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

[2-(2,6-Dichloro-phenyl)-ethyl]-(3-iodo-benzyl)-carbamic acid tert-butyl ester (506 mg), tetrabutylammonium chloride (280 mg), sodium bicarbonate (210 mg), allyl alcohol (100 μL) and toluene (20 mL) were charged to a flask, followed by palladium acetate (10 mg) and the resultant mixture heated to 80° C., under nitrogen for 5 hours. On cooling, the reaction was filtered, the filtrate diluted with toluene and extracted sequentially, twice with water, once with brine, dried (magnesium sulfate) and evaporated. Purification on silica, eluting with a gradient of iso-hexane/ethyl acetate [4:1 to 2:1], gave the subtitle product as an oil (300 mg).

Workup

  1. temperatureOn cooling
  2. filtrationthe reaction was filtered
  3. additionthe filtrate diluted with toluene
  4. extractionextracted sequentially, twice with water, once with brine
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated
  7. customPurification on silica
  8. washeluting with a gradient of iso-hexane/ethyl acetate [4:1 to 2:1]

Sources & evidence

ORD record
ord-afa6b8abe1114c1ab5991068c3143061
Source dataset
uspto-grants-2011_05
Patent number
US07951954B2

Reaction notes

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