Reaction #335604

Reaction equation

fluorescein isothiocyanate

6-ethylenedioxy-1-hexylamine

→

fluorescein

Yield 72.0%

Solvents

pyridine

Conditions

Workup

1. 1
   ConcentrationAfter concentrating the solution under reduced pressure
2. 2
   Otherthe crude product was purified by flash chromatography

Procedure

A mixture of 10.8 mg (0.28 mmoles) of fluorescein isothiocyanate and 23 mg (0.14 mmoles) of 6-ethylenedioxy-1-hexylamine in 1.5 ml of dry pyridine was stirred at 23° C. for one hour. After concentrating the solution under reduced pressure, the crude product was purified by flash chromatography using 10% methanol in methylene chloride to afford 11 mg (72%) of fluorescein-linker acetal. This was quantitatively converted to the aldehyde by treatment with 80% aqueous acetic acid at 37° C. for 3 hours followed by lyophilization.

Source