1,4-Cyclohexadiene → 1-(5-Hydroxymethyl-1,3,4-oxadiazol-2-yl)-7-phenoxy-heptan-1-one

HRID 512007Notes

Reaction equation

HRID 512007 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([C:16]1[O:17][C:18]([CH2:21][O:22]CC2C=CC=CC=2)=[N:19][N:20]=1)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CC=CCC=1>CC(O)=O.CO.[Pd]>[OH:22][CH2:21][C:18]1[O:17][C:16]([C:14](=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N:20][N:19]=1

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 250186077-(Phenoxy)-1-(5-benzyloxymethyl-1,3,4-oxadiazol-2-yl)-heptan-1-one

Product 1

HCID 250186081-(5-Hydroxymethyl-1,3,4-oxadiazol-2-yl)-7-phenoxy-heptan-1-oneYield 25%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 10129899Acetic acid methanolSolvent

Procedure

To a stirred suspension of 73.1 (80 mg, 0.2 mmol) and Pd/C (160 mg) in AcOH/MeOH (1:10 mixture, 5 mL) at 45° C. was added 1,4-cyclohexadiene (304 mg, 4 mmol) over a period of 30 min. The mixture was stirred for an additional 2 h at the same temperature. The catalyst was removed by filtration through celite and the filtrate was evaporated under reduced pressure. The residue was purified through a column of silica, eluting with 45% ethyl acetate in petroleum ether to give 74.1 as a white solid (m p 83-85° C.) in 25% yield (15 mg).

Workup

  1. customThe catalyst was removed by filtration through celite
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe residue was purified through a column of silica
  4. washeluting with 45% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-96367140a96b42809dc0bde9522eb54c
Source dataset
uspto-grants-2015_08
Patent number
US09102622B2

Reaction notes

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