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

Participants

Role	Name	HCID	Charge
Reactant	4-(3-Bromo-propyl)-5-methyl-2-phenyl-oxazole	HCID 12093266	—
Reactant	6-(5-Methyl-2-phenyl-oxazol-4-yl)-hex-2-yn-1-ol	HCID 12093269	—
Product	4-(6-Bromo-hex-4-ynyl)-5-methyl-2-phenyl-oxazole	HCID 12093270	80%

Reaction Steps

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).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06696474B2
Source dataset	uspto-grants-2004_02
ORD ID	ord-27b0b1f396ae4cb487941920b07da631
Source note	uspto-grants-2004_02