2-(5-Bromo-4-methyl-2-thienyl)-4-[4-[4-(1-imidazolyl)butyl]phenoxymethyl]oxazole → 4-[4-[4-(1-Imidazolyl)butyl]phenoxymethyl]-2-(4-methyl-2-thienyl)oxazole

HRID 322453Notes

Reaction equation

HRID 322453 reaction equation
Br[C:2]1[S:6][C:5]([C:7]2[O:8][CH:9]=[C:10]([CH2:12][O:13][C:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22][CH2:23][N:24]4[CH:28]=[CH:27][N:26]=[CH:25]4)=[CH:16][CH:15]=3)[N:11]=2)=[CH:4][C:3]=1[CH3:29]>[Zn]>[N:24]1([CH2:23][CH2:22][CH2:21][CH2:20][C:17]2[CH:16]=[CH:15][C:14]([O:13][CH2:12][C:10]3[N:11]=[C:7]([C:5]4[S:6][CH:2]=[C:3]([CH3:29])[CH:4]=4)[O:8][CH:9]=3)=[CH:19][CH:18]=2)[CH:28]=[CH:27][N:26]=[CH:25]1

Participants

3

Reactant 1

HCID 220096732-(5-Bromo-4-methyl-2-thienyl)-4-[4-[4-(1-imidazolyl)butyl]phenoxymethyl]oxazole

Product 1

HCID 220097214-[4-[4-(1-Imidazolyl)butyl]phenoxymethyl]-2-(4-methyl-2-thienyl)oxazoleYield 89%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

In substantially the same manner as in Working Example 138, 2-(5-bromo-4-methyl-2-thienyl)-4-[4-[4-(1-imidazolyl)butyl]phenoxymethyl]oxazole was reduced by zinc powder to give 4-[4-[4-(1-imidazolyl)butyl]phenoxymethyl]-2-(4-methyl-2-thienyl)oxazole. The yield was 89%. Recrystallization from ethyl acetate-hexane gave colorless prisms, mp 77-78° C.

Sources & evidence

ORD record
ord-14fdd96524634192a24d56ce39ea3ebe
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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