Acetylene → 1,5-Decadiyne

Temperature

80 °C

Wang iodopolystyrene (100 mg), synthesized as described in Example 1, was dissolved in a solvent mixture of DMF/distilled water/TEA (9:1:1) (5 mL) and allowed to swell for 30 minutes at room temperature. 1,5-decadiyne (100 mg) in DMF (2 mL) was added to the polymer bead suspension. Potassium carbonate (50 mg, 0.36 mm) and tetrabutylammonium bromide (50 mg, 0.16 mM) were then added and the suspension was stirred under argon atmosphere for 30 minutes. Tetrakis (triphenylphosphine) palladium (O) (25 mg, 0.02 mM) was added rapidly. The reaction mixture was heated to 80° C. and agitated at that temperature under an argon atmosphere for 16 hours and allowed to cool to room temperature. When the mixture had reached room temperature, a saturated solution of ammonium acetate (5 mL) was added and the mixture agitated at room temperature for 30 minutes. DME (5 mL) was added and the mixture was agitated for an additional 30 minutes, transferred to a fritted filter funnel and washed sequentially with distilled water, DMF, distilled water, 2 N HCl, distilled water, DMF, distilled water, methanol, DCM and methanol (50 mL of each which was allowed to equilibrate for 10 minutes between washes). The product was dried under vacuum to produce a tagged bead containing only one Raman active acetylene tag.

1. distillationdistilled water/TEA (9:1:1) (5 mL)
2. addition1,5-decadiyne (100 mg) in DMF (2 mL) was added to the polymer bead suspension
3. additionPotassium carbonate (50 mg, 0.36 mm) and tetrabutylammonium bromide (50 mg, 0.16 mM) were then added
4. additionTetrakis (triphenylphosphine) palladium (O) (25 mg, 0.02 mM) was added rapidly
5. stirringagitated at that temperature under an argon atmosphere for 16 hours
6. temperatureto cool to room temperature
7. customhad reached room temperature
8. additiona saturated solution of ammonium acetate (5 mL) was added
9. stirringthe mixture agitated at room temperature for 30 minutes
10. additionDME (5 mL) was added
11. stirringthe mixture was agitated for an additional 30 minutes
12. customtransferred to a fritted filter funnel
13. washwashed sequentially with distilled water, DMF
14. distillationdistilled water, 2 N HCl
15. distillationdistilled water, DMF
16. distillationdistilled water, methanol, DCM and methanol (50 mL of each which
17. waitto equilibrate for 10 minutes between washes
18. customThe product was dried under vacuum
19. customto produce a tagged bead

ORD record

ord-010e4d09f82f4a348d6b578d3f3ac1ad

Source dataset

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06355490B1