Pyridine → HCID 19363554, compound

HRID 850326Notes

Reaction equation

HRID 850326 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7][O:8][CH2:9][CH2:10][C:11]([CH2:13][OH:14])=[CH2:12])=[CH:5][CH:4]=1.N1C=CC=CC=1.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(OCC)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][CH2:9][CH2:10][C:11]([CH2:13][O:14][C:23](=[O:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH2:12])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 11287493HCID 11287493, compound

Product 1

HCID 19363554HCID 19363554, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Combine 4-(p-methoxybenzyloxy)-2-hydroxymethylbut-1-ene (0.77 g, 3.46 mmol) with pyridine (3 mL) and add dropwise benzoyl chloride (603 μL, 5.2 mmol). Stir the mixture at room temperature for 20 hours. Dilute the reaction mixture with diethyl ether (100 mL) and washed 3X with saturated sodium bicarbonate solution, dry over MgSO4 and concentrate in vacuo. Chromatograph on silica gel eluting with 1/9 ethyl acetate/hexane to give the title compound as an oil. Rf =0.28, silica gel, 1/9 ethyl acetate/hexane.

Workup

  1. washwashed 3X with saturated sodium bicarbonate solution
  2. dry with materialdry over MgSO4
  3. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-7961459913db4af19f3db26fd83ae030
Source dataset
uspto-grants-2000_01
Patent number
US06017923

Reaction notes

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