Piperidine → 5-{5-[2-(2-Bromoethenyl)-4-(4,5-dihydro-2-oxazolyl)phenoxy]pentyl}-3-methylisoxazole

HRID 359853

Reaction equation

HRID 359853 reaction equation
N1CCCCC1.[CH2:7]([Li])[CH2:8][CH2:9][CH3:10].[Br-:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([C:34]1[CH:51]=[C:50]([C:52]2[O:53][CH2:54][CH2:55][N:56]=2)C=C[C:35]=1[O:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42]1[O:46][N:45]=[C:44]([CH3:47])[CH:43]=1)=O>CCOCC.O1CCCC1>[Br:12][CH:7]=[CH:8][C:9]1[CH:10]=[C:50]([C:52]2[O:53][CH2:54][CH2:55][N:56]=2)[CH:51]=[CH:34][C:35]=1[O:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42]1[O:46][N:45]=[C:44]([CH3:47])[CH:43]=1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 5271233Benzaldehyde, 5-(4,5-dihydro-2-oxazolyl)-2-((5-(3-methyl-5-isoxazolyl)pentyl)oxy)-HCID 22470945Triphenylphosphine bromideHCID 178418339Butyllithium

Product 1

HCID 542384105-{5-[2-(2-Bromoethenyl)-4-(4,5-dihydro-2-oxazolyl)phenoxy]pentyl}-3-methylisoxazole

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.255 g piperidine in 100 ml ether at 0° under nitrogen was added 12 ml n-butyllithium (1.23 m) followed by 5 g triphenylphosphine bromide. The mixture was then stirred two hours at room temperature and 4.78 g 5-{5-[2-formyl-4-(4,5-dihydro-2-oxazolyl)phenoxy]pentyl}-3-methylisoxazole (Example 70) in 35 ml tetrahydrofuran was added dropwise. The reaction mixture was kept overnight at room temperature and worked up by chromatography to give 0.53 g 5-{5-[2-(2-bromoethenyl)-4-(4,5-dihydro-2-oxazolyl)phenoxy]pentyl}-3-methylisoxazole, colorless needles, m.p. 94°-96° C. after recrystallization from isopropyl acetate and hexane.

Workup

  1. waitThe reaction mixture was kept overnight at room temperature

Sources & evidence

ORD record
ord-03bdfa59e2994649a9f6b2c8e9c6b9b0
Source dataset
uspto-grants-1991_03
Patent number
US05002960

Linked notes

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