4-(3-Bromo-propyl)-5-methyl-2-phenyl-oxazole → 4-(6-Bromo-hex-4-ynyl)-5-methyl-2-phenyl-oxazole

HRID 2121699Notes

Reaction equation

HRID 2121699 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][CH2:15][C:16]#[C:17][CH2:18]O.[Br:20]CCCC1N=C(C2C=CC=CC=2)OC=1C>>[Br:20][CH2:18][C:17]#[C:16][CH2:15][CH2:14][CH2:13][C:3]1[N:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:6][C:2]=1[CH3:1]

Participants

3

Reactant 2

HCID 120932664-(3-Bromo-propyl)-5-methyl-2-phenyl-oxazoleHCID 120932696-(5-Methyl-2-phenyl-oxazol-4-yl)-hex-2-yn-1-ol

Product 1

HCID 120932704-(6-Bromo-hex-4-ynyl)-5-methyl-2-phenyl-oxazoleYield 80%

Procedure

Alcohol 1-8 (1.2 g, 4.7 mmol) was treated in a manner similar to the preparation of bromide 1-5. Chromatography with 10% EtOAc/Hexanes gave the product 1-9 as a colorless oil (1.7 g) in 80% yield. NMR CDCl3 (δ): 7.97 (2H, m); 7.40 (3H, m); 3.93 (2H, s); 2.60 (2H, m); 2.34 (3H, s); 2.28 (2H, m); 1.89 (2H, m).

Sources & evidence

ORD record
ord-27b0b1f396ae4cb487941920b07da631
Source dataset
uspto-grants-2004_02
Patent number
US06696474B2

Reaction notes

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