Potassium Hydroxide → 5-{5-[2,6-Dimethyl-4-(4-oxazolyl)phenoxy]pentyl}-3-methylisoxazole

HRID 359852Notes

Reaction equation

HRID 359852 reaction equation
[O:1]1[CH:5]=[C:4]([C:6]2[CH:11]=[C:10]([CH3:12])[C:9]([OH:13])=[C:8]([CH3:14])[CH:7]=2)[N:3]=[CH:2]1.Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]1[O:25][N:24]=[C:23]([CH3:26])[CH:22]=1.[OH-].[K+]>>[CH3:14][C:8]1[CH:7]=[C:6]([C:4]2[N:3]=[CH:2][O:1][CH:5]=2)[CH:11]=[C:10]([CH3:12])[C:9]=1[O:13][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]1[O:25][N:24]=[C:23]([CH3:26])[CH:22]=1.[C:21]([O:13][CH:9]([CH3:8])[CH3:10])(=[O:25])[CH3:20].[CH3:5][CH2:4][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 135440465-(5-Bromopentyl)-3-methylisoxazoleHCID 200641234-(4-Oxazolyl)-2,6-dimethylphenol

Product 2

HCID 200640885-{5-[2,6-Dimethyl-4-(4-oxazolyl)phenoxy]pentyl}-3-methylisoxazoleHCID 22034165Hexane isopropyl acetate

Procedure

5-{5-[2,6-Dimethyl-4-(4-oxazolyl)phenoxy]pentyl}-3-methylisoxazole [XXIX; n=5, R1 and R2 =CH3 ], m.p. 47°-48° C. (pale yellow powder from isopropyl acetate/hexane) was prepared in 38% yield by reacting 4-(4-oxazoly)-2,6-dimethylphenol, m.p. 113°-115° C., with 5-(5-bromopentyl)-3-methylisoxazole according to the procedure of Example 9(c) but using potassium hydroxide in place of potassium carbonate.

Sources & evidence

ORD record
ord-8a34e375d54a4debbfb9c8543af1dca8
Source dataset
uspto-grants-1991_03
Patent number
US05002960

Reaction notes

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