2-Aminophenol → 3-[2-(Benzoxazol-2-yl)ethenyl]-5-ethyl-6-benzyloxymethyl-2-benzyloxypyridine

HRID 2081536Notes

Reaction equation

HRID 2081536 reaction equation
[Cl-].[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[CH2:11][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.NC1C=CC=CC=1O.CC1C=CC(C)=C(N)C=1O.[H-].[Na+].[CH2:51]([O:58][C:59]1[N:66]=[C:65]([CH2:67][O:68][CH2:69][C:70]2[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=2)[C:64]([CH2:76][CH3:77])=[CH:63][C:60]=1[CH:61]=O)[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1>O1CCCC1.C(O)(=O)C>[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[CH:11]=[CH:61][C:60]1[C:59]([O:58][CH2:51][C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=2)=[N:66][C:65]([CH2:67][O:68][CH2:69][C:70]2[CH:71]=[CH:72][CH:73]=[CH:74][CH:75]=2)=[C:64]([CH2:76][CH3:77])[CH:63]=1

Participants

8

Reactant 5

HCID 58012-AminophenolHCID 24758Sodium hydrideHCID 150363212-Amino-3,6-dimethylphenolHCID 19769114[(1,3-Benzoxazol-2-yl)methyl](triphenyl)phosphanium chlorideHCID 197691192-Benzyloxy-5-ethyl-6-benzyloxymethylnicotinaldehyde

Product 1

HCID 678542803-[2-(Benzoxazol-2-yl)ethenyl]-5-ethyl-6-benzyloxymethyl-2-benzyloxypyridine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of [(benzoxazol-2-yl)methyl]triphenylphosphonium chloride (1.77 g, 4.12 mmol) (prepared using substantially the same procedures described in Example 5, but substituting 2-aminophenol and the intermediate thereof for the 2,5-dimethyl-6-aminophenol and its corresponding intermediate used therein), in dry tetrahydrofuran (20 mL), under a nitrogen atmosphere, was added 60% NaH/mineral oil (0.42 g, 10 mmol). After 0.5 hour a solution of 2-benzyloxy-5-ethyl-6-benzyloxymethylnicotinaldehyde (1.44 g, 4.0 mmol) in tetrahydrofuran (10 mL) was added and the reaction mixture was refluxed for 23 hours. The reaction was cooled, neutralized with acetic acid and partitioned between water and chloroform. The chloroform layer was washed with NaHCO3 solution, dried, filtered through a pad of charcoal and evaporated. This material was dissolved in chloroform and flash chromatographed through silica gel to give pure product as a yellow oil. The product was a mixture of cis and trans olefins.

Workup

  1. customprepared
  2. temperaturethe reaction mixture was refluxed for 23 hours
  3. temperatureThe reaction was cooled
  4. custompartitioned between water and chloroform
  5. washThe chloroform layer was washed with NaHCO3 solution
  6. customdried
  7. filtrationfiltered through a pad of charcoal
  8. customevaporated
  9. dissolutionThis material was dissolved in chloroform
  10. customflash chromatographed through silica gel
  11. customto give pure product as a yellow oil

Sources & evidence

ORD record
ord-f2aca578e4294c438761801cb74a803b
Source dataset
uspto-grants-1993_02
Patent number
US05185251

Reaction notes

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