Methyl 5-methyl-3-isoxazolepropanoate → 5-{8-[2-Chloro-4-(4,5-dihydro-2-oxazolyl)phenoxy]octyl}-3-methylisoxazole

HRID 359819Notes

Reaction equation

HRID 359819 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[O:10][CH2:11][CH2:12][N:13]=2)[CH:5]=[CH:6][C:7]=1[OH:8].Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[O:27][N:26]=[C:25]([CH3:28])[CH:24]=1.CC1ON=C(CCC(OC)=O)C=1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[O:10][CH2:11][CH2:12][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[O:27][N:26]=[C:25]([CH3:28])[CH:24]=1

Participants

4

Reactant 3

HCID 573461Methyl 5-methyl-3-isoxazolepropanoateHCID 135440485-(8-Bromooctyl)-3-methylisoxazoleHCID 1356214654,5-Dihydro-2-(3-chloro-4-hydroxyphenyl)oxazole

Product 1

HCID 52730995-{8-[2-Chloro-4-(4,5-dihydro-2-oxazolyl)phenoxy]octyl}-3-methylisoxazole

Procedure

5-{8-[2-Chloro-4-(4,5-dihydro-2-oxazolyl)phenoxy]octyl}-3-methylisoxazole [IX; R=CH3, R2, R3, R4, R5 and R6 =H, R1 =2-Cl, Y=(CH2)8, oxazole at 4-position] was prepared from 4,5-dihydro-2-(3-chloro-4-hydroxyphenyl)oxazole (Example 13b) and 5-(8-bromooctyl)-3-methylisoxazole (Example 18a) according to the procedure of Example 9, part (d), and was obtained in the form of a colorless solid, m.p. 63°-64° C. when recrystallized from ether.

Workup

  1. customwas obtained in the form of a colorless solid, m.p. 63°-64° C. when
  2. customrecrystallized from ether

Sources & evidence

ORD record
ord-78517ee747f743dc96ac68e1eff6611f
Source dataset
uspto-grants-1991_03
Patent number
US05002960

Reaction notes

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