A practical approach for the preparation of monofunctional azulenyl squaraine dye

Tetrahedron Letters

Volumn 44, Issue 20, 2003, Pages 3975-3978

  Pham, Wellington ^a   Weissleder, Ralph ^a   Tung, Ching Hsuan ^a  

^a MASSACHUSETTS GENERAL HOSPITAL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (METHOXYXCARBONYL) 2 METHYLAZULENE; 2H 3 METHOXYCARBONYLCYCLOHEPTA[B]FURAN 2 ONE; 3 (2 METHYLAZULEN 4 YL)PROPIONIC ACID; AZULENE; AZULENE DERIVATIVE; AZULENYL SQUARAINE DYE; CARBOXYLIC ACID; CHEMICAL COMPOUND; CYCLOHEPTATRIENE; DYE; ETHER DERIVATIVE; FLUOROCHROME; FURANONE DERIVATIVE; PROPIONIC ACID DERIVATIVE; SQUARIC ACID; UNCLASSIFIED DRUG;

ABSORPTION; ARTICLE; CHEMICAL PARAMETERS; CHEMICAL PROCEDURES; CYCLOADDITION; FLUORESCENCE; HIGH TEMPERATURE; METHYLATION; POLYMERIZATION; PRESSURE;

EID: 0037433799     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00819-0     Document Type: Article

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20. max=548 nm. 9 . A 2.5 M solution of n-BuLi (846 μL, 2.12 mmol) was added dropwise to a solution of 2,4-dimethyl azulene 8 (220 mg, 1.41 mmol) and diisopropyl amine (316 μL, 2.26 mmol) in ether (10 mL) at -40°C then reaction mixture was warmed up to 0°C for 30 min. A solution of bromoacetic acid (195.90 mg, 1.41 mmol) in ether (1 mL) was added dropwise to the reaction mixture after cooling the flask to -40°C. The reaction was stirred overnight as the temperature slowly raised up to room temperature. The reaction mixture was poured onto ice-cold water (30 mL) and the unreacted starting material 8 was extracted with ether (2×10 mL). The aqueous phase was acidified by 2 M HCl (20ml), and extracted with ether (20 ml).