Methyl 5-methyl-3-isoxazolepropanoate → 5-Oxazolemethanol, 4,5-dihydro-2-(4-((7-(3-methyl-5-isoxazolyl)heptyl)oxy)phenyl)-

HRID 359825Notes

Reaction equation

HRID 359825 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH2:10][CH2:11][N:12]=2)=[C:4](C)[CH:3]=1.Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]1[O:26][N:25]=[C:24]([CH3:27])[CH:23]=1.C[C:29]1[O:33]N=C(CCC(OC)=O)C=1>>[OH:33][CH2:29][CH:10]1[O:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([O:1][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]3[O:26][N:25]=[C:24]([CH3:27])[CH:23]=3)=[CH:7][CH:6]=2)=[N:12][CH2:11]1

Participants

4

Reactant 3

HCID 573461Methyl 5-methyl-3-isoxazolepropanoateHCID 133169675-(7-Bromoheptyl)-3-methylisoxazoleHCID 1356214774,5-Dihydro-2-(4-hydroxy-2-methylphenyl)oxazole

Product 1

HCID 52721595-Oxazolemethanol, 4,5-dihydro-2-(4-((7-(3-methyl-5-isoxazolyl)heptyl)oxy)phenyl)-Yield 27%

Procedure

5-{7-[4-(4,5-Dihydro-2-oxazolyl)-3-methylphenoxy]heptyl}-3-methylisoxazole [IX; R=CH3, R2, R3, R4, R5 and R6 =H, R1 =3-CH3, Y=(CH2)7, oxazole at 4-position] was prepared from 4,5-dihydro-2-(4-hydroxy-2-methylphenyl)oxazole and 5-(7-bromoheptyl)-3-methylisoxazole according to the procedure of Example 9, part (d) and was obtained in 27% yield as a colorless solid, m.p. 58°-59° C. when recrystallized from an isopropyl acetate-hexane mixture.

Workup

  1. customwas obtained in 27% yield as a colorless solid, m.p. 58°-59° C. when
  2. customrecrystallized from an isopropyl acetate-hexane mixture

Sources & evidence

ORD record
ord-4420cc32b4b64cbd8f5284fd79ece101
Source dataset
uspto-grants-1991_03
Patent number
US05002960

Reaction notes

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