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 (0) (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. customsynthesized
2. distillationdistilled water/TEA (9:1:1) (5 mL)
3. addition1,5-decadiyne (100 mg) in DMF (2 mL) was added to the polymer bead suspension
4. additionPotassium carbonate (50 mg, 0.36 mm) and tetrabutylammonium bromide (50 mg, 0.16 mM) were then added
5. additionTetrakis (triphenylphosphine) palladium (0) (25 mg, 0.02 mM) was added rapidly
6. stirringagitated at that temperature under an argon atmosphere for 16 hours
7. temperatureto cool to room temperature
8. customhad reached room temperature
9. additiona saturated solution of ammonium acetate (5 mL) was added
10. stirringthe mixture agitated at room temperature for 30 minutes
11. additionDME (5 mL) was added
12. stirringthe mixture was agitated for an additional 30 minutes
13. customtransferred to a fritted filter funnel
14. washwashed sequentially with distilled water, DMF
15. distillationdistilled water, 2 N HCl
16. distillationdistilled water, DMF
17. distillationdistilled water, methanol, DCM and methanol (50 mL of each which
18. waitto equilibrate for 10 minutes between washes
19. customThe product was dried under vacuum
20. customto produce a tagged bead

ORD record

ord-2b569f65e1bd4b75852f475c5269b3e0

Source dataset

uspto-grants-2001_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06274385B1